Microbiocidal oxadiazole derivatives

ABSTRACT

Compounds of the formula (I) wherein the substituents are as defined in claim  1 , useful as a pesticides, especially fungicides.

The present invention relates to microbiocidal oxadiazole derivatives,eg, as active ingredients, which have microbiocidal activity, inparticular, fungicidal activity. The invention also relates toagrochemical compositions which comprise at least one of the oxadiazolederivatives and to uses of the oxadiazole derivatives or compositions inagriculture or horticulture for controlling or preventing infestation ofplants, harvested food crops, seeds or non-living materials byphytopathogenic microorganisms, preferably fungi.

WO 2015/185485 describes the use of substituted oxadiazoles forcombating phytopathogenic fungi.

According to the present invention, there is provided a compound offormula (I):

wherein

n is 1 or 2;

A¹ represents N or CR¹, wherein R¹ represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy;

A² represents N or CR², wherein R² represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy;

A³ represents N or CR³, wherein R³ represents hydrogen or halogen;

A⁴ represents N or CR⁴, wherein R⁴ represents hydrogen or halogen; and

wherein 0 or 1 or 2 of A¹, A², A³ and A⁴ are N;

R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl, halogen,cyano, trifluoromethyl and difluoromethyl, or

R⁵ and R⁶ together with the carbon atom they share form a cyclopropyl;

Z is selected from Z¹, Z², Z³, Z⁴, Z⁵ or Z⁶; wherein

Z¹ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—C bond, whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR⁷, C(O), or S(O)₂, with the proviso that theheterocycle cannot contain 2 contiguous atoms selected from O and S;

Z² represents a heteroaryl linked to C(R⁵)(R⁶) via a C—C bond, whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring which contains1 nitrogen atom in the ring system and optionally comprises 1, 2, or 3additional ring members independently selected from the group consistingof O, S, N, or NR⁷;

R⁷ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, C₁₋₄alkylsulfonyl,N—C₁₋₂alkylaminosulfonyl, or N,N-diC₁₋₂alkylaminosulfonyl; and

wherein for Z¹ and Z², the heterocyclyl or heteroaryl moiety isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R⁸;

R⁸ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino;

Z³ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR⁹ or C(═N—O—C₁₋₄alkyl), with the proviso thatthe heterocycle cannot contain 2 contiguous atoms selected from O and S;

Z⁴ represents a heteroaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heteroaryl moiety is a 5-membered aromatic ring which contains 1 to4 nitrogen atoms in the ring system;

R⁹ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl; and

wherein for Z³ and Z⁴, the heterocyclyl or heteroaryl moiety isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R¹⁰;

wherein R¹⁰ represents:

(i) cyano, halogen, hydroxy, amino, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄alkoxyC₁₋₄alkyl,C₁₋₄alkylsulfanyl, C₁₋₄haloalkoxy, C₁₋₄alkylsulfanyl, C₁₋₄alkylsulfinyl,C₁₋₄alkylsulfonyl, C₁₋₄haloalkylsulfanyl, C₃₋₄alkenyloxy,C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, formyl,hydroxycarbonyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,C₁₋₄alkylcarbonylamino, aminocarbonyl, N—C₁₋₄alkylaminocarbonyl,N—C₂₋₄alkenylaminocarbonyl, N—C₂₋₄alkynylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, N-morpholinoaminocarbonyl,N—C₁₋₄alkoxyaminocarbonyl, N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl, phenylcarbonyloxyC₁₋₄alkyl,phenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxy,C₁₋₄haloalkylcarbonyloxy, C₁₋₄alkylcarbonyloxyC₁₋₄alkyl,C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, (C₁₋₄alkyl)₃Si—; or

(ii) —C(O)N(R^(a))(R^(b)), wherein:

R^(a) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl,C₃₋₅alkenyl, C₃₋₅-alkynyl, aminoC₁₋₄alkyl, N—C₁₋₄alkylaminoC₁₋₄alkyl,N,N-diC₁₋₄alkylaminoC₁₋₄alkyl, formyl, C₁₋₄alkylcarbonyl,C₁₋₄cycloalkylcarbonyl, C₁₋₄haloalkylcarbonyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₃₋₄alkyl,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₄alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₄alkyl, C₁₋₄alkylsulfanylC₁₋₄alkyl,C₁₋₄alkylsulfonyl, C₁₋₄alkylsulfonylC₁₋₄alkyl,C₁₋₄alkylsulfonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, orC₁₋₄haloalkylcarbonylaminoC₁₋₄alkyl, and

R^(b) is hydrogen, hydroxyl, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl,C₃₋₄cycloalkyl, C₃₋₄cycloalkylC₁₋₂alkyl, C₁₋₄alkoxy, C₃₋₄alkenyloxy,C₃₋₄haloalkenyloxy, C₃₋₄alkynyloxy; or

R^(a) and R^(b) together with the nitrogen atom to which they arebonded, form a 4-, 5- or 6-membered cycle optionally containing anadditional heteroatom or group selected from O, S, S(O)₂, C(O) andNR^(c), wherein R^(c) is hydrogen, methyl, methoxy, formyl or acyl; or

(iii) —C(O)O—R^(d), wherein:

R^(d) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₂alkoxyC₁₋₄alkyl,C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₅alkenyl, C₃₋₄haloalkenyl,C₃₋₄alkenyloxyC₁₋₄alkyl, C₃₋₅alkynyl, C₃₋₄alkynyloxyC₁₋₄alkyl,N—C₁₋₃alkylaminoC₁₋₄alkyl, N,N-di-C₁₋₃alkylaminoC₁₋₄alkyl,C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl or C₁₋₄alkylcarbonylaminoC₁₋₄alkyl; or

wherein for Z⁴, the heteroaryl moiety is optionally substituted by 1substituent selected from R¹¹ and further optionally substituted by 1 or2 substituents, which may be the same or different, selected from R¹⁰;

wherein R¹¹ represents:

(i) C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl,N—C₃₋₈cycloalkylaminocarbonyl, N—C₃₋₈cycloalkylC₁₋₂alkylaminocarbonyl,phenyl, phenylC₁₋₂alkyl, phenoxyC₁₋₂alkyl, phenylC₁₋₂alkylsulfanyl,heteroaryl, heteroarylC₁₋₂alkyl, heteroaryloxyC₁₋₂alkyl,N-heteroarylaminocarbonyl, heterocyclylcarbonyl, wherein the heteroarylmoiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N, O and S, benzodioxolyl, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl, heterocyclyl and benzodioxolylmoieties are optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R¹²; or

(ii) —C(O)N(R^(e))(R^(f)), wherein:

R^(e) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein theheterocyclyl moiety is a 4- to 6-membered non-aromatic ring whichcomprises 1, 2, or 3 ring members independently selected from the groupconsisting of O, S, N or S(O)₂, with the proviso that the heterocyclecannot contain 2 contiguous atoms selected from O and S, heteroaryl,heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S,

and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety isoptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from hydroxyl, amino, formyl, acyl, cyano, halogen,methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionallysubstituted by 1 or 2 groups which are oxo (═O), and

R^(f) is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy C₁₋₄haloalkyl, C₃₋₄alkenyl,C₃₋₄alkynyl, C₃₋₄cycloalkyl, C₃₋₄cycloalkylC₁₋₂alkyl; or

(iii) —C(O)O—R⁹, wherein:

R^(g) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein theheterocyclyl moiety is a 4- to 6-membered non-aromatic ring whichcomprises 1, 2, or 3 ring members independently selected from the groupconsisting of O, S, N or S(O)₂, with the proviso that the heterocyclecannot contain 2 contiguous atoms selected from O and S, heteroaryl,heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S,

and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety isoptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, orthe cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or2 groups which are oxo (═O); or

(iv) (C₁₋₄alkyl)-O—N═C(R^(h))—, (C₁₋₄haloalkyl)-O—N═C(R^(h))—,(C₂₋₄alkenyl)-O—N═C(R^(h)), (C₂₋₄alkynyl)-O—N═C(R^(h))—,benzyl-O—N═C(R^(h))—, wherein R^(h) is hydrogen or methyl;

R¹² is cyano, fluoro, chloro, bromo, methyl, ethyl, formyl, methoxy,ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy orethoxycarbonyl;

Z⁵ represents a heterobicyclyl linked to C(R⁵)(R⁶) via a C—N bond,wherein the heterobicyclyl moiety is a 7- to 10-membered saturated,partially saturated or partially aromatic fused ring system whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR¹³, C(O) or S(O)₂, with the proviso that theheterobicyclyl cannot contain 2 contiguous atoms selected from O and S;

Z⁶ represents a heterodiaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterdioaryl moiety is a 9-membered di-aromatic system whichcontains 1 to 4 nitrogen atoms in the ring system;

R¹³ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl; and

wherein for Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety isoptionally substituted by 1, 2, 3 or 4 substituents, which may be thesame or different, selected from R¹⁴;

R¹⁴ is cyano, halogen, hydroxy, formyl, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, cyanoC₁₋₄alkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy,C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino,N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, or C₁₋₄alkoxycarbonylamino, andadditionally oxo (═O) for Z⁵; or

wherein for Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety isoptionally substituted by 1 substituent selected from R¹⁵ and furtheroptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from R¹⁴;

R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, whereinphenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from chloro,fluoro, bromo, methyl, ethyl, methoxy and ethoxy; or

a salt or an N-oxide thereof.

Surprisingly, it has been found that the novel compounds of formula (I)have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

According to a second aspect of the invention, there is provided anagrochemical composition comprising a fungicidally effective amount of acompound of formula (I).

According to a third aspect of the invention, there is provided a methodof controlling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a fungicidally effective amountof a compound of formula (I), or a composition comprising this compoundas active ingredient, is applied to the plants, to parts thereof or thelocus thereof.

According to a fourth aspect of the invention, there is provided the useof a compound of formula (I) as a fungicide. According to thisparticular aspect of the invention, the use may exclude methods for thetreatment of the human or animal body by surgery or therapy.

As used herein, the term “halogen” or “halo” refers to fluorine(fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo),preferably fluorine, chlorine or bromine.

As used herein, cyano means a —CN group.

As used herein, amino means an —NH₂ group.

As used herein, hydroxy means an —OH group.

As used herein, the term “C₁₋₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond. Theterms “C₁₋₄alkyl” and “C₁₋₂alkyl” are to be construed accordingly. A“C₁₋₆alkylene”, C₁₋₄alkylene” or “C₁₋₂alkylene” group refers to thecorresponding definition of C₁₋₆alkyl, C₁₋₄alkyl or C₁₋₂alkyl,respectively, except that such radical is attached to the rest of themolecule by two single bonds. Examples of C₁₋₆alkyl include, but are notlimited to, methyl, ethyl, iso-propyl, n-propyl and t-butyl.

As used herein, the term “C₁₋₄alkoxy” refers to a radical of the formula—OR_(a) where R_(a) is a C₁₋₄alkyl radical as generally defined above.Examples of C₁₋₄alkoxy include, but are not limited to, methoxy, ethoxyand propoxy.

As used herein, the term “C₁₋₄alkoxyC₁₋₄alkyl” refers to radical of theformula R_(b)—O—R_(a)— where R_(b) is a C₁₋₄alkyl radical as generallydefined above, and R_(a) is a C₁₋₄alkylene radical as generally definedabove.

As used herein, the term “C₁₋₄alkylsulfanyl” refers to a radical of theformula —SR_(a) where R_(a) is a C₁₋₄alkyl radical as generally definedabove.

As used herein, the term “C₁₋₄alkylsulfinyl” refers to a radical of theformula —S(O)R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₄alkylsulfonyl” refers to a radical of theformula —S(O)₂R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₂₋₄alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond that can be of either the(E)- or (Z)-configuration, having from two to four carbon atoms, whichis attached to the rest of the molecule by a single bond. The term“C₃₋₄alkenyl” is to be construed accordingly. Examples of C₂₋₄alkenylinclude, but are not limited to, ethenyl and prop-1-enyl.

As used herein, the term “C₂₋₄alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from two to fourcarbon atoms, and which is attached to the rest of the molecule by asingle bond. The term “C₃₋₄alkynyl” is to be construed accordingly.Examples of C₂₋₄alkynyl include, but are not limited to, ethynyl,prop-1-ynyl, propargyl (prop-2-ynyl), but-1-ynyl.

As used herein, the term “C₃₋₄alkenyloxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₃₋₄alkenyl radical as generallydefined above.

As used herein, the term “C₃₋₄alkynyloxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₃₋₄alkynyl radical as generallydefined above.

As used herein, the term “C₁₋₄alkoxycarbonyl” refers to a radical of theformula —C(O)OR_(a) where R_(a) is a C₁-C₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₄alkylcarbonyl” refers to a radical of theformula —C(O)R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “formyl” refers to a radical of the formula—C(O)H.

As used herein, the term “hydroxycarbonyl” refers to a radical of theformula —C(O)OH.

As used herein, the term “C₁₋₄alkylcarbonyloxy” refers to a radical ofthe formula —OC(O)R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₄haloalkoxy” refers to a C₁₋₄alkoxy groupas defined above substituted by one or more of the same or differenthalogen atoms. Examples of C₁₋₄haloalkoxy include, but are not limitedto, fluoromethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy.

As used herein, the term “C₁₋₄haloalkyl” refers to a C₁₋₄alkyl radicalas generally defined above substituted by one or more of the same ordifferent halogen atoms. Examples of C₁₋₄haloalkyl include, but are notlimited to fluoromethyl, fluoroethyl, difluoromethyl and trifluormethyl.

As used herein, the term “C₁₋₄haloalkylsulfanyl” refers to aC₁₋₄alkylsulfanyl radical as generally defined above substituted by oneor more of the same or different halogen atoms.

As used herein, the term “C₂₋₄haloalkenyl” refers to a C₂₋₄alkenylradical as generally defined above substituted by one or more of thesame or different halogen atoms.

As used herein, the term “C₃₋₈cycloalkyl” refers to a stable, monocyclicor bi-cyclic ring radical which is saturated or partially unsaturatedand contains 3 to 8 carbon atoms. C₃₋₆cycloalkyl is to be construedaccordingly. Examples of C₃₋₈cycloalkyl include, but are not limited to,cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

As used herein, the term “C₃₋₈cycloalkylC₁₋₂alkyl” refers to aC₃₋₈cycloalkyl ring as defined above attached to the rest of themolecule by a C₁₋₂alkylene radical as defined above. The terms“C₃₋₆cycloalkylC₁₋₂alkyl” and “C₃₋₄cycloalkylC₁₋₂alkyl” are to beconstrued accordingly. Examples of C₃₋₈cycloalkylC₁₋₂alkyl include, butare not limited to cyclopropyl-methyl, cyclobutyl-ethyl, andcyclopentyl-propyl.

As used herein, the term “C₃₋₈cycloalkylaminocarbonyl” refers to aradical of the formula —C(O)NR_(a) where R_(a) is a C₃₋₈cycloalkylradical as generally defined above.

As used herein, the term “N—C₃₋₈cycloalkylC₁₋₂alkylaminocarbonyl” refersto a radical of the formula —C(O)NR_(a) where R_(a) is aC₃₋₆-cycloalkylC₁₋₂alkylene radical as defined above.

As used herein, the term “C₁₋₄alkoxycarbonylamino” refers to a radicalof the formula —NH—C(O)—O—R_(a) where R_(a) is a C₁₋₄alkyl radical asdefined above.

As used herein, the term “C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl” refers to aradical of the formula —R_(a)C(O)NHR_(b) where R_(a) is a C₁₋₄alkoxyradical as defined above and R_(b) is a C₁₋₄alkylene radical as definedabove.

As used herein, the term “C₁₋₄alkylcarbonyloxy” refers to a radical ofthe formula —OC(O)R_(a) where R_(a) is a C₁₋₄alkyl as generally definedabove.

As used herein, the term “C₁₋₄alkylcarbonyloxyC₁₋₄alkyl” refers to aradical of the formula —R_(a)OC(O)R_(b) where R_(a) is a C₁₋₄alkyleneradical as generally defined above and R_(b) is a C₁₋₄alkyl as generallydefined above.

As used herein, oxo means an ═O group, eg, a ketonyl (—C(O)—), sulfinyl(—S(O)—) or sulfonyl (—S(O)₂—) oxygen.

As used herein, aminocarbonyl means an —C(O)NH₂ radical.

As used herein, the term “N—C₁₋₄alkylamino” refers to a radical of theformula —NH—R_(a) where R_(a) is a C₁₋₄alkyl radical as defined above.

As used herein, the term “N,N-diC₁₋₄alkylamino” refers to a radical ofthe formula —N(R_(a))R_(a) where each R_(a) is a C₁₋₄alkyl radical,which may be the same or different, as defined above.

As used herein, the term “N,N-diC₁₋₄alkylaminocarbonyl” refers to aradical of the formula —C(O)NR_(a)(R_(a)) where each R_(a) is aC₁₋₄alkyl radical, which may be the same or different, as generallydefined above.

As used herein, the term “N—C₁₋₄alkylaminocarbonyl” refers to a radicalof the formula —C(O)NHR_(a) where R_(a) is a C₁₋₄alkyl radical asgenerally defined above.

As used herein, the term “N—C₂₋₄alkenylaminocarbonyl” refers to aradical of the formula —C(O)NHR_(a) where R_(a) is a C₂₋₄alkenyl radicalas generally defined above.

As used herein, the term “N—C₂₋₄alkynylaminocarbonyl” refers to aradical of the formula —C(O)NHR_(a) where R_(a) is a C₂₋₄alkynyl radicalas generally defined above.

As used herein, the term “N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl” refers toa radical of the formula —C(O)NHR_(a)OR_(b) where R_(a) is aC₁₋₄alkylene radical as generally defined above, and R_(b) is aC₁₋₄alkyl radical as generally defined above.

As used herein, the term “N—C₁₋₄alkoxyaminocarbonyl, refers to a radicalof the formula —C(O)NHOR_(a) where R_(a) is a a C₁₋₄alkyl radical asgenerally defined above.

As used herein, the term “N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl, refersto a radical of the formula —C(O)N(R_(a))OR_(b) where R_(a) is aC₁₋₄alkyl radical as generally defined above, and R_(b) is a C₁₋₄alkylradical (same or different to R_(a)) as generally defined above.

As used herein, the term “phenylcarbonyloxyC₁₋₄alkyl” refers to aradical of the formula R_(b)—C(O)OR_(a)— where R_(b) is a phenylradical, and R_(a) is a C₁₋₄alkylene radical as generally defined above.

As used herein, the term “phenylcarbonylaminoC₁₋₄alkyl” refers to aradical of the formula R_(b)—C(O)NHR_(a)— where R_(b) is a phenylradical, and R_(a) is a C₁₋₄alkylene radical as generally defined above.

As used herein, the term “C₁₋₄alkylcarbonylaminoC₁₋₄alkyl” refers to aradical of the formula R_(b)—C(O)NHR_(a)— where R_(b) is a C₁₋₄alkylradical, and R_(a) is a C₁₋₄alkylene radical as generally defined above.

As used herein, the term “phenylC₁₋₂alkyl” refers to a phenyl ringattached to the rest of the molecule by a C₁₋₂alkylene radical asdefined above.

As used herein, the term “phenoxyC₁₋₂alkyl” refers to a phenoxy ringattached to the rest of the molecule by a C₁₋₂alkylene radical asdefined above.

As used herein, the term “phenylC₁₋₂alkylsulfanyl” refers to an —SR_(a)radical wherein R_(a) is a phenylC₁₋₂alkyl radical as defined above.

As used herein, the term “aryl” refers to an aromatic ring systemconsisting solely of carbon and hydrogen atoms which may be mono-, bi-or tricyclic. Examples of such ring systems include phenyl,naphthalenyl, anthracenyl, indenyl or phenanthrenyl.

As used herein, the term “heteroaryl” (unless defined otherwise) refersto a 5- or 6-membered aromatic monocyclic ring radical which comprises1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen andsulfur. The heteroaryl radical may be bonded via a carbon atom or aheteroatom.

Examples of heteroaryl include, but are not limited to, furyl, pyrrolyl,thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl,isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl orpyridyl.

As used herein, the term “heteroarylC₁₋₂alkyl” refers to a heteroarylring attached to the rest of the molecule by a C₁₋₂alkylene radical asdefined above.

As used herein, the term “heteroaryloxyC₁₋₂alkyl” refers to a radical ofthe formula —R_(a)OR_(b) where R_(a) is a C₁₋₂alkylene radical asgenerally defined above, and R_(b) is a heteroaryl radical as definedabove.

As used herein, the term “heterodiaryl” (unless defined otherwise)refers to a stable 9- or 10-membered bicyclic aromatic ring system whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen,oxygen and sulfur. The heterodiaryl radical may be bonded to the rest ofthe molecule via a carbon atom or heteroatom. Examples of heterodiarylinclude, but are not limited to, indolyl, indazolyl, benzimidazolyl,pyrrolopyridinyl or triazolopyridinyl.

As used herein, the term “heterocyclyl” or “heterocyclic” (unlessdefined otherwise) refers to a stable 4-, 5- or 6-membered non-aromaticmonocyclic ring radical which comprises 1, 2, or 3, heteroatomsindividually selected from nitrogen, oxygen and sulfur. The heterocyclylradical may be bonded to the rest of the molecule via a carbon atom orheteroatom. Examples of heterocyclyl include, but are not limited to,azetidinyl, oxetanyl, pyrrolinyl, pyrrolidyl, thietanyl,tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl,piperazinyl, tetrahydropyranyl, morpholinyl or perhydroazepinyl.

As used herein, the term “heterocyclylC₁₋₆alkyl” refers to aheterocyclyl ring attached to the rest of the molecule by a C₁₋₆alkyleneradical as defined above. The terms “heterocyclylC₁₋₄alkyl” and“heterocyclylC₁₋₂alkyl” are to be construed accordingly.

As used herein, the term “benzodioxolyl” means a radical as follows:

The presence of one or more possible asymmetric carbon atoms in acompound of formula (I) means that the compounds may occur in chiralisomeric forms, i.e., enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formula (I) is intended to include all those possible isomericforms and mixtures thereof. The present invention includes all thosepossible isomeric forms and mixtures thereof for a compound of formula(I).

Likewise, formula (I) is intended to include all possible tautomers(including lactam-lactim tautomerism and keto-enol tautomerism) wherepresent. The present invention includes all possible tautomeric formsfor a compound of formula (I).

In each case, the compounds of formula (I) according to the inventionare in free form, in covalently hydrated form, in oxidized form as anN-oxide or in salt form, e.g., an agronomically usable or agrochemicallyacceptable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991.

The following list provides definitions, including preferreddefinitions, for substituents n, A¹, A², A³, A⁴, R¹, R², R³, R⁴, R⁵, R⁶,Z (Z¹, Z², Z³, Z⁴, Z⁵, Z⁶), R⁷, R⁸, R⁹, R¹⁰ (including R^(a), R^(b),R^(c), R^(d), R^(e), R^(f), R^(g), R^(h)), R¹¹, R¹², R¹³, R¹⁴, and R¹⁵,with reference to the compounds of formula (I). For any one of thesesubstituents, any of the definitions given below may be combined withany definition of any other substituent given below, or elsewhere inthis document.

n is 1 or 2. In one embodiment of the invention, n is 1. In anotherembodiment of the invention, n is 2.

When n is 2, Z is linked to the rest of the molecule by the C(R⁵)(R⁶)fragment least proximal to the A¹ to A⁴ ring system.

In another embodiment of the invention, there is provided a compound offormula (I): wherein

A¹ represents N or CR¹, wherein R¹ represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy;

A² represents N or CR², wherein R² represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy;

A³ represents N or CR³, wherein R³ represents hydrogen or halogen;

A⁴ represents N or CR⁴, wherein R⁴ represents hydrogen or halogen; and

wherein no more than two of A¹ to A⁴ are N;

R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl, halogen,cyano, trifluoromethyl and difluoromethyl; or R⁵ and R⁶ together withthe carbon atom to which they are attached form a cyclopropyl;

-   -   Z is selected from Z¹, Z², Z³, Z⁴, Z⁵ or Z⁶; wherein    -   Z¹ represents a heterocycle linked to C(R⁵)(R⁶) via a C—C bond,        wherein the heterocycle moiety is a 5- or 6-membered        non-aromatic ring which contains 1 nitrogen in the ring system        and optionally comprises 0, 1, 2, or 3 additional ring members        independently selected from the group consisting of O, S, N,        NR⁷, C(O), or S(O)₂, with the proviso that the heterocycle        cannot contain 2 consecutive atoms selected from O and S;

Z² represents a heteroaryl linked to C(R⁵)(R⁶) via a C—C bond, whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring which contains1 nitrogen atom in the ring system and optionally comprises 0, 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, or NR⁷;

R⁷ is C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl;

-   -   wherein for Z¹ and Z², the heterocyclyl or heteroaryl moiety is        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁸;    -   R⁸ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,        C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy,        C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy,        N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl,        C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino,        N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl or        C₁₋₄alkoxycarbonylamino;

Z³ represents a heterocycle linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, or NR⁹, with the proviso that the heterocyclecannot contain 2 consecutive atoms selected from O and S;

Z⁴ represents a heteroaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heteroaryl moiety is a 5-membered aromatic ring which contains 1 to4 nitrogen atoms in the ring system;

R⁹ is C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl; and

wherein for Z³ and Z⁴, the heterocyclyl or heteroaryl moiety isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R¹⁰;

R¹⁰ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy,C₁₋₄alkoxyC₁₋₄alkyl, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy,N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, C₁₋₄alkoxycarbonylamino,C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, phenylcarbonyloxyC₁₋₄alkylphenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxy,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, (C₁₋₄alkyl)₃Si—;

wherein for Z⁴, any heteroaryl moieties are optionally substituted by 1substituent selected from R¹¹ and are further optionally substituted by1 or 2 substituents selected from R¹⁰;

R¹¹ represents C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, phenyloxyC₁₋₂alkyl, heteroaryl, heteroarylC₁₋₂alkyl,heteroaryloxyC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹²;

R¹² represents hydrogen, cyano, fluoro, chloro, bromo, methyl, ethyl,methoxy, ethoxy, difluoromethyl, trifluoromethyl or difluoromethoxy;

Z⁵ represents a heterobicyclyl linked to C(R⁵)(R⁶) via a C—N bond,wherein the heterobicyclyl moiety is a 7- to 10-membered saturated,partially saturated or partially aromatic fused ring system whichcontains 1 nitrogen in the ring system and optionally comprises 0, 1, 2,or 3 additional ring members independently selected from the groupconsisting of O, S, N, or NR¹³, C(O) or S(O)₂, with the proviso that theheterobicyclyl cannot contain 2 consecutive atoms selected from O and S;

Z⁶ represents a heterdioaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterdioaryl moiety is a 9-membered di-aromatic system whichcontains 1 to 4 nitrogen atom in the ring system;

R¹³ is C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl;

wherein for Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R¹⁴;

R¹⁴ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino.

In other embodiments of the invention:

A¹ represents N or CR¹, wherein R¹ represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy. Preferably, A¹ represents CR¹, wherein R¹ is hydrogen,halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxyor difluoromethoxy. More preferably, R¹ is hydrogen or halogen, and evenmore preferably, R¹ is hydrogen.

A² represents N or CR², wherein R² represents hydrogen, halogen, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy. Preferably, A² represents CR², wherein R² is hydrogen,halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,ethoxy, or difluoromethoxy. More preferably, R² is hydrogen or halogen,and even more preferably, R² is hydrogen.

A³ represents N or CR³, wherein R³ represents hydrogen or halogen.Preferably, A³ represents CR³, wherein R³ is hydrogen or halogen. Morepreferably, R³ is hydrogen or fluoro, and even more preferably, R³ ishydrogen.

A⁴ represents N or CR⁴, wherein R⁴ represents hydrogen or halogen.Preferably, A⁴ represents CR⁴, wherein R⁴ is hydrogen or halogen. Morepreferably, R⁴ is hydrogen or fluoro, and even more preferably, R⁴ ishydrogen.

In the compounds according to Formula (I), no more than two (ie, 0, 1 or2) of A¹, A², A³ and A⁴ are N.

In some embodiments of the invention, A¹ is N or CR¹ wherein R¹represents hydrogen, chloro, fluoro, methyl, methoxy or trifluoromethyl,and A², A³ and A⁴ are C—H. Preferably, A¹ is N and A², A³ and A⁴ areC—H; or A¹ is C—F and A², A³ and A⁴ are C—H; or A¹ is C—Cl and A², A³and A⁴ are C—H; or A¹, A², A³ and A⁴ are C—H. More preferably, A¹, A²,A³ and A⁴ are C—H. In other embodiments of the invention, A³ is CR³ andR³ is halogen (eg, fluoro or chloro), and A¹, A² and A⁴ are C—H.

In some embodiments of the invention, the 6-membered ring comprising A¹to A⁴ is a phenyl (where A¹, A², A³ and A⁴ are C—H), a pyridinyl (whereA¹ is N and A², A³ and A⁴ are C—H, or A³ is N and A¹, A² and A⁴ areC—H), a fluorophenyl (where A¹ is C—F and A², A³ and A⁴ are C—H, or A³is C—F and A¹, A² and A⁴ are C—H) or a difluorophenyl (eg, where A¹ andA² are C—F and A³ and A⁴ are C—H, or A and A³ are C—F and A² and A⁴ areC—H) group.

R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl, halogen,cyano, trifluoromethyl and difluoromethyl, or R⁵ and R⁶ together withthe carbon atom they share form a cyclopropyl. R⁵ is hydrogen,C₁₋₄alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, andpreferably, hydrogen, C₁₋₄alkyl, halogen or cyano. R⁶ is hydrogen,C₁₋₄alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, andpreferably, hydrogen, C₁₋₄alkyl, halogen or cyano. Preferably, R⁵ ishydrogen and R⁶ is C₁₋₄alkyl, preferably methyl or ethyl. Morepreferably, R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl.

Z is selected from Z¹, Z², Z³, Z⁴, Z⁵ or Z⁶.

In some embodiments of the invention, Z is Z¹. In other embodiments ofthe invention, Z is Z². In other embodiments of the invention, Z is Z³.In other embodiments of the invention, Z is Z⁴. In other embodiments ofthe invention, Z is Z⁵. In other embodiments of the invention, Z is Z⁶.Preferably, Z is Z⁴ or Z⁶.

Z¹ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—C bond, whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR⁷, C(O), or S(O)₂, with the proviso that theheterocycle cannot contain 2 contiguous atoms selected from O and S. Z¹may be selected from pyrrolidinyl, piperidinyl, imidazolidinyl,pyrazolidinyl, piperazinyl, oxazolidinyl, isooxazolidinyl,4,5-dihydrooxazolyl, morpholinyl, thiazolidinyl, thiazolinyl,thiomorpholinyl.

Preferably, Z¹ optionally comprises 1 additional ring member selectedfrom O, S, N, NR⁷, C(O), or S(O)₂, and more preferably, O or S.According to an embodiment of the invention, Z¹ is a heterocyclyl moietycomprising a 5- or 6-membered non-aromatic ring with 1 nitrogen in thering system.

Z² represents a heteroaryl linked to C(R⁵)(R⁶) via a C—C bond, whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring which contains1 nitrogen atom in the ring system and optionally comprises 1, 2, or 3additional ring members independently selected from the group consistingof O, S, N, or NR⁷. Z² may be selected from pyrrolyl, pyrazolyl,imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrazinyl,pyrimidinyl, pyridazinyl, triazinyl. Preferably, Z² optionally comprises1 or 2 additional ring members selected from O, S, N, or NR⁷. Morepreferably, Z² is pyridinyl, in particular, pyridin-2-yl, pyridin-3-ylor pyridin-4-yl.

According to an embodiment of the invention, Z² is a heteroaryl moietywhich is a 5- or 6-membered aromatic ring with 1 nitrogen in the ringsystem.

For Z¹ and Z², the heterocyclyl or heteroaryl moiety is optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁸. Preferably, for Z¹ and Z², the heterocyclylor heteroaryl moiety is optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R⁸. More preferably,for Z¹ and Z², the heterocyclyl or heteroaryl moiety is optionallysubstituted by 1 substituent selected from R⁸.

R⁷ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, C₁₋₄alkylsulfonyl,N—C₁₋₂alkylaminosulfonyl, or N,N-diC₁₋₂alkylaminosulfonyl. Preferably,R⁷ is hydrogen or methyl.

R⁸ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino. Preferably, R⁸ represents cyano, halogen,hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl,C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy.

More preferably, R⁸ represents cyano, chloro, fluoro, hydroxy, methyl,ethyl, difluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluormethoxy.

Z³ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR⁹ or C(═N—O—C₁₋₄alkyl), with the proviso thatthe heterocycle cannot contain 2 contiguous atoms selected from O and S.Preferably, Z³ optionally comprises 1 additional ring member selectedfrom O, S, N, or NR⁹. Z³ may be selected from pyrrolidinyl, piperidinyl,imidazolidinyl, pyrazolidinyl, piperazinyl, oxazolidinyl,isooxazolidinyl, 4,5-dihydrooxazolyl, morpholinyl, thiazolidinyl,thiazolinyl, thiomorpholinyl.

According to an embodiment of the invention, Z³ is a heterocycle moietycomprising a 5- or 6-membered non-aromatic ring with one nitrogen in thering system.

Z⁴ represents a heteroaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heteroaryl moiety is a 5-membered aromatic ring which contains 1 to4 nitrogen atoms in the ring system. Preferably, Z⁴ is pyrrolyl,pyrazolyl, imidazolyl, triazolyl, tetrazolyl.

In particular, Z⁴ (optionally substituted according to the invention)may be selected from:

More preferably, Z⁴ is pyrazol-1-yl or triazolyl. When Z⁴ is triazolyl,it may be 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-4-yl or1,2,4-triazol-1-yl, and most preferably, 1,2,4-triazol-1-yl or1,2,3-triazol-1-yl.

Z⁴ may be a heteroaryl moiety which is a 5-membered aromatic ring with asingle nitrogen in the ring system. However, in some embodiments, Z⁴ mayfurther comprise 1 or 2 additional ring members selected from O, S andN.

For Z³ and Z⁴, the heterocyclyl or heteroaryl moiety is optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹⁰, or for Z⁴, the heteroaryl moiety isoptionally substituted by 1 substituent selected from R¹¹ and furtheroptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from R¹⁰.

Preferably, for Z⁴, the heteroaryl moiety is optionally substituted by 1substituent or 2 substituents, which may be the same or different,selected from R¹⁰, or the heteroaryl moiety is optionally substituted by1 substituent selected from R¹¹ and further optionally substituted by 1substituent selected from R¹⁰. For Z⁴, the heteroaryl moiety mayoptionally be substituted by 1 substituent selected from R¹⁰, or theheteroaryl moiety may optionally be substituted by 1 substituentselected from R¹¹.

R⁹ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl. Preferably, R⁹ is hydrogen or methyl.

R¹⁰ represents (i), (ii) or (iii), wherein:

(i) cyano, halogen, hydroxy, amino, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄alkoxyC₁₋₄alkyl,C₁₋₄haloalkoxy, C₁₋₄alkylsulfanyl, C₁₋₄alkylsulfinyl, C₁₋₄alkylsulfonyl,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,formyl, hydroxycarbonyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,C₁₋₄alkylcarbonylamino, aminocarbonyl, N—C₁₋₄alkylaminocarbonyl,N—C₂₋₄alkenylaminocarbonyl, N—C₂₋₄alkynylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, N-morpholinoaminocarbonyl,N—C₁₋₄alkoxyaminocarbonyl, N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl, phenylcarbonyloxyC₁₋₄alkyl,phenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxy,C₁₋₄haloalkylcarbonyloxy, C₁₋₄alkylcarbonyloxyC₁₋₄alkyl,C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, (C₁₋₄alkyl)₃Si—; or

(ii) —C(O)N(R^(a))(R^(b)), wherein:

R^(a) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl,C₃₋₅alkenyl, C₃₋₅alkynyl, aminoC₁₋₄alkyl, N—C₁₋₄alkylaminoC₁₋₄alkyl,N,N-diC₁₋₄alkylaminoC₁₋₄alkyl, formyl, C₁₋₄alkylcarbonyl,C₃₋₄cycloalkylcarbonyl, C₁₋₄haloalkylcarbonyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₄alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₄alkyl, C₁₋₄alkylsulfanylC₁₋₄alkyl,C₁₋₄alkylsulfonyl, C₁₋₄alkylsulfonylC₁₋₄alkyl,C₁₋₄alkylsulfonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,C₁₋₄haloalkylcarbonylaminoC₁₋₄alkyl, and

R^(b) is hydrogen, hydroxyl, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl,C₃₋₄cycloalkyl, C₃₋₄cycloalkylC₁₋₂alkyl, C₁₋₄alkoxy, C₃₋₄alkenyloxy,C₃₋₄haloalkenyloxy, C₃₋₄alkynyloxy; or

R^(a) and R^(b) together with the nitrogen atom to which they arebonded, form a 4-, 5- or 6-membered cycle optionally containing anadditional heteroatom or group selected from O, S, S(O)₂, C(O) andNR^(c), wherein R^(c) is hydrogen, methyl, methoxy, formyl or acyl; or

(iii) —C(O)O—R^(d), wherein:

R^(d) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl,hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₂alkoxyC₁₋₄alkyl,C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₅alkenyl, C₃₋₄haloalkenyl,C₃₋₄alkenyloxyC₁₋₄alkyl, C₃₋₅alkynyl, C₃₋₄alkynyloxyC₁₋₄alkyl,N—C₁₋₃alkylaminoC₁₋₄alkyl, N,N-di-C₁₋₃alkylaminoC₁₋₄alkyl,C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl or C₁₋₄alkylcarbonylaminoC₁₋₄alkyl.

Preferably, R¹⁰ (particularly, when Z is Z⁴) represents cyano, halogen,hydroxy, amino, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄alkoxy,C₁₋₄alkoxyC₁₋₄alkyl, C₁₋₄alkylsulfanyl, C₁₋₄haloalkylsulfanyl,N,N-diC₁₋₄alkylamino, formyl, hydroxycarbonyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, aminocarbonyl, N—C₁₋₄alkylaminocarbonyl,N—C₂₋₄alkynylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl,N-morpholinoaminocarbonyl, N—C₁₋₄alkoxyaminocarbonyl,N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl,N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl, phenylcarbonylaminoC₁₋₄alkyl,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylcarbonylaminoC₁₋₄alkyl,(C₁₋₄alkyl)₃Si—.

More preferably, R¹⁰ (particularly, when Z is Z⁴) represents cyano,fluoro, chloro, bromo, iodo, hydroxy, amino, methyl, ethyl, n-propyl,iso-propyl, n-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl,methoxy, ethoxy, ethoxymethyl, methoxyethyl, methylsulfanyl,ethylsulfanyl, n-propylsulfanyl, difluoromethylsulfanyl,trifluoromethylsulfanyl, dimethylamino, formyl, hydroxycarbonyl,methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,i-propoxycarbonyl, t-butoxycarbonyl, aminocarbonyl, methylaminocarbonyl,ethylaminocarbonyl, propynylaminocarbonyl (includingpropargylaminocarbonyl), morpholinoaminocarbonyl,N-methoxyaminocarbonyl, N-methyl-N-methoxyaminocarbonyl,N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,t-butoxycarbonylaminomethyl, methoxyethylaminocarbonyl,phenylcarbonylamino(dimethyl)methyl, methylcarbonyloxymethyl,methylcarbonylaminoethyl, trimethylsilyl.

In some preferred embodiments of the invention, R¹⁰ is selected fromhydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,i-propoxycarbonyl, t-butoxycarbonyl, aminocarbonyl, methylaminocarbonyl,ethylaminocarbonyl, propargylaminocarbonyl, N-morpholinoaminocarbonyl,N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,N-methyl-N-methoxyaminocarbonyl or N-methoxyaminocarbonyl. In somefurther preferred embodiments, R¹⁰ is selected from hydroxycarbonyl,methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl,methylaminocarbonyl and ethylaminocarbonyl.

In other embodiments of the invention, R¹⁰ is cyano, halogen, hydroxy,C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl,C₁₋₄alkoxy, C₁₋₄alkyl, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy,N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl, C₁₋₄alkoxycarbonylamino,C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, phenylcarbonyloxyC₁₋₄alkylphenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxy,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, or (C₁₋₄alkyl)₃Si—.

R¹¹ represents (i), (ii), (iii) or (iv), wherein:

(i) C₃₋₈cycloalkyl, C₃-acycloalkylC₁₋₂alkyl,N—C₃₋₈cycloalkylaminocarbonyl, N—C₃₋₈cycloalkylC₁₋₂alkylaminocarbonyl,phenyl, phenylC₁₋₂alkyl, phenoxyC₁₋₂alkyl, phenylC₁₋₂alkylsulfanyl,heteroaryl, heteroarylC₁₋₂alkyl, heteroaryloxyC₁₋₂alkyl,N-heteroarylaminocarbonyl, heterocyclylcarbonyl, wherein the heteroarylmoiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N, O and S, benzodioxolyl, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl, heterocyclyl and benzodioxolylmoieties are optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R¹²; or

(ii) —C(O)N(R^(e))(R^(f)), wherein:

R^(e) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein theheterocyclyl moiety is a 4- to 6-membered non-aromatic ring whichcomprises 1, 2, or 3 ring members independently selected from the groupconsisting of O, S, N or S(O)₂, with the proviso that the heterocyclecannot contain 2 contiguous atoms selected from O and S, heteroaryl,heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S,

and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety isoptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from hydroxyl, amino, formyl, acyl, cyano, halogen,methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionallysubstituted by 1 or 2 groups which are oxo (═O), and

R^(f) is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy C₁₋₄haloalkyl, C₃₋₄alkenyl,C₃₋₄alkynyl, C₃₋₄cycloalkyl, or C₃₋₄cycloalkylC₁₋₂alkyl; or

(iii) —C(O)O—R⁹, wherein:

R^(g) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein theheterocyclyl moiety is a 4- to 6-membered non-aromatic ring whichcomprises 1, 2, or 3 ring members independently selected from the groupconsisting of O, S, N or S(O)₂, with the proviso that the heterocyclecannot contain 2 contiguous atoms selected from O and S, heteroaryl,heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S,

and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety isoptionally substituted by 1 or 2 substituents, which may be the same ordifferent, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, orthe cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or2 groups which are oxo (═O); or

(iv) (C₁₋₄alkyl)-O—N═C(R^(h))—, (C₁₋₄haloalkyl)-O—N═C(R^(h))—,(C₂₋₄alkenyl)-O—N═C(R^(h)), (C₂₋₄alkynyl)-O—N═C(R^(h))—,benzyl-O—N═C(R^(h))—, wherein R^(h) is hydrogen or methyl;

Preferably, R¹¹ (particularly, when Z is Z⁴) represents cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, phenyl, cyclopropylaminocarbonyl,cyclopropylmethylaminocarbonyl, phenoxymethyl, benzylsulfanyl,pyrazolyl, imidazolyl, thienyl, pyridinyl, pyridinyloxymethyl,benzodioxolyl.

Preferably, R¹¹ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl, phenyl,phenylC₁₋₂alkyl, phenyloxyC₁₋₂alkyl, heteroaryl, heteroarylC₁₋₂alkyl,heteroaryloxyC₁₋₂alkyl, heterocyclyl, or heterocyclylC₁₋₆alkyl.

R¹² represents cyano, fluoro, chloro, bromo, methyl, ethyl, formyl,methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy orethoxycarbonyl. Preferably, R¹² is cyano, fluoro, chloro, bromo, methyl,ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl ordifluoromethoxy.

Z⁵ represents a heterobicyclyl linked to C(R⁵)(R⁶) via a C—N bond,wherein the heterobicyclyl moiety is a 7- to 10-membered saturated,partially saturated or partially aromatic fused ring system whichcontains 1 nitrogen in the ring system and optionally comprises 1, 2, or3 additional ring members independently selected from the groupconsisting of O, S, N, NR¹³, C(O) or S(O)₂, with the proviso that theheterobicyclyl cannot contain 2 contiguous atoms selected from O and S.Z⁵ may be selected from cyclopentapyrrolyl, tetrahydropurinyl.

Z⁶ represents a heterdioaryl linked to C(R⁵)(R⁶) via a C—N bond, whereinthe heterdioaryl moiety is a 9-membered di-aromatic system whichcontains 1 to 4 nitrogen atoms in the ring system. Preferably, Z⁶represents a heterdioaryl which contains 1, 2 or 3 nitrogen atoms in thering system. Z⁶ may be selected from indolyl, benzimidazolyl,benzotriazolyl (including benzotriazol-1-yl and benzotriazol-2-yl),indazolyl, pyrrolopyridinyl.

For Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety is optionallysubstituted by 1, 2, 3 or 4 substituents, which may be the same ordifferent, selected from R¹⁴, or for Z⁵ and Z⁶, the heterobicyclyl orheterodiaryl moiety is optionally substituted by 1 substituent selectedfrom R¹⁵ and further optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R¹⁴. For Z⁶, theheterodiaryl moiety may be optionally substituted by 1 or 2substituents, which may be the same or different, selected from R¹⁴, orfor Z⁶, the heterodiaryl moiety may optionally be substituted by 1substituent selected from R¹⁵ and further optionally substituted by 1substituent selected from R¹⁴

R¹³ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, orN,N-diC₁₋₄alkylaminocarbonyl. Preferably, R¹³ is hydrogen or methyl.

R¹⁴ represents cyano, halogen, hydroxy, formyl, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, cyanoC₁₋₄alkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy,C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino,N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl or C₁₋₄alkoxycarbonylamino, andadditionally oxo (═O) for Z⁵. Preferably, R¹⁴ represents fluoro, chloro,bromo, methyl, ethyl, formyl, difluoromethyl, trifluoromethyl,cyanomethyl, methoxy, ethoxy, methylcarbonyl, methoxycarbonyl,ethoxycarbonyl.

Preferably, R¹⁴ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino.

R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, whereinphenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from chloro,fluoro, bromo, methyl, ethyl, methoxy and ethoxy.

Preferably, the compound according to Formula (I) is selected from acompound 1.1 to 1.312 listed in Table T1 (below).

Preferably, in a compound according to formula (I) of the invention:

-   -   n is 1;    -   A¹ is N or CR¹ wherein R¹ represents hydrogen, chloro, fluoro,        methyl, methoxy or trifluoromethyl;    -   A², A³ and A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl;    -   Z is Z⁴ selected from pyrrolyl, pyrazolyl, imidazolyl,        triazolyl, tetrazolyl and is optionally substituted by 1, 2 or 3        substituents, which may be the same or different, selected from        R¹⁰, or is optionally substituted by 1 substituent selected from        R¹¹ and further optionally substituted by 1 or 2 substituents        selected from R¹⁰;    -   R¹⁰ represents cyano, fluoro, chloro, bromo, iodo, hydroxy,        amino, methyl, ethyl, n-propyl, iso-propyl, n-butyl, s-butyl,        t-butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,        ethoxymethyl, methoxyethyl, methylsulfanyl, ethylsulfanyl,        n-propylsulfanyl, difluoromethylsulfanyl,        trifluoromethylsulfanyl, formyl, hydroxycarbonyl,        methylcarbonyl, methoxycarbonyl, ethoxycarbonyl,        i-propoxycarbonyl, t-butoxycarbonyl, methylaminocarbonyl,        ethylaminocarbonyl, propynylaminocarbonyl,        dimethylaminocarbonyl, t-butoxycarbonylaminomethyl,        methoxyethylaminocarbonyl, phenylcarbonylamino(dimethyl)methyl,        methylcarbonyloxymethyl, methylcarbonylaminoethyl,        trimethylsilyl;    -   R¹¹ is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl,        cyclopropylaminocarbonyl, cyclopropylmethylaminocarbonyl,        phenoxymethyl, benzylsulfanyl, imidazolyl, thienyl, pyridinyl,        pyridinyloxymethyl, benzodioxolyl, wherein any of said        cycloalkyl, phenyl, heteroaryl and benzodioxolyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R¹²; and    -   R¹² is cyano, fluoro, chloro, bromo, methyl, ethyl, formyl,        methoxy, ethoxy, difluoromethyl, trifluoromethyl or        difluoromethoxy.

More preferably,

-   -   n is 1;    -   A¹ is N and A², A³ and A⁴ are C—H; or A¹ is C—F and A², A³ and        A⁴ are C—H; or A¹ is C—Cl and A², A³ and A⁴ are C—H; or A¹, A²,        A³ and A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   Z is Z⁴ selected from Z⁴ is pyrazol-1-yl or triazolyl, and is        optionally substituted by 1 or 2 substituents, which may be the        same or different, selected from R¹⁰, or is optionally        substituted by 1 substituent selected from R¹¹ and further        optionally substituted by 1 substituent selected from R¹⁰;    -   R¹⁰ represents cyano, fluoro, chloro, bromo, iodo, hydroxy,        amino, methyl, ethyl, n-propyl, iso-propyl, n-butyl, s-butyl,        t-butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,        ethoxymethyl, methoxyethyl, methylsulfanyl, ethylsulfanyl,        n-propylsulfanyl, difluoromethylsulfanyl,        trifluoromethylsulfanyl, formyl, hydroxycarbonyl,        methylcarbonyl, methoxycarbonyl, ethoxycarbonyl,        i-propoxycarbonyl, t-butoxycarbonyl, methylaminocarbonyl,        ethylaminocarbonyl, propynylaminocarbonyl,        dimethylaminocarbonyl, t-butoxycarbonylaminomethyl,        methoxyethylaminocarbonyl, phenylcarbonylamino(dimethyl)methyl,        methylcarbonyloxymethyl, methylcarbonylaminoethyl,        trimethylsilyl;    -   R¹¹ is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl,        cyclopropylaminocarbonyl, cyclopropylmethylaminocarbonyl,        phenoxymethyl, benzylsulfanyl, imidazolyl, thienyl, pyridinyl,        pyridinyloxymethyl, benzodioxolyl, wherein any of said        cycloalkyl, phenyl, heteroaryl and benzodioxolyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R¹²; and    -   R¹² is cyano, fluoro, chloro, bromo, methyl, ethyl, formyl,        methoxy, ethoxy, difluoromethyl, trifluoromethyl or        difluoromethoxy.

Even more preferably,

-   -   n is 1;    -   A¹, A², A³ and A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   Z is Z⁴ selected from pyrazol-1-yl, 1,2,3-triazol-1-yl or        1,2,4-triazol-1-yl, wherein pyrazol-1-yl is optionally        substituted by 1 substituent selected from R¹⁰ or R¹¹, wherein        R¹⁰ is hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl,        i-propoxycarbonyl, t-butoxycarbonyl, methylaminocarbonyl or        ethylaminocarbonyl and R¹¹ is cyclopropylaminocarbonyl,        cyclobutylaminocarbonyl, cyclopentylaminocarbonyl or        cyclohexylaminocarbonyl, and 1,2,3-triazol-1-yl or        1,2,4-triazol-1-yl is optionally substituted by 1 substituent        selected from R¹⁰ or R¹¹, wherein R¹⁰ is cyano, ethynyl, fluoro,        chloro, methyl, ethyl, trifluoromethyl, methoxy, ethoxycarbonyl        or ethoxymethyl, and R¹¹ is cyclopropyl.

Preferably, in a compound according to formula (I) of the invention:

-   -   n is 1;    -   A¹ is N or CR¹ wherein R¹ represents hydrogen, chloro, fluoro,        methyl, methoxy or trifluoromethyl;    -   A², A³ and A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl;    -   Z is Z⁶ selected from indolyl, indazolyl, benzimidazolyl,        pyrrolopyridinyl or triazolopyridinyl and is optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R¹⁴, or is optionally substituted by 1        substituent selected from R¹⁵ and further optionally substituted        by 1 or 2 substituents selected from R¹⁴;    -   R¹⁴ represents fluoro, chloro, bromo, methyl, ethyl, formyl,        difluoromethyl, trifluoromethyl, cyanomethyl, methoxy, ethoxy,        methylcarbonyl, methoxycarbonyl, ethoxycarbonyl; and    -   R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl,        wherein phenoxy and phenylsulfanyl are optionally substituted by        1, 2 or 3 substituents, which may be the same or different,        selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and        ethoxy.

More preferably,

-   -   n is 1;    -   A¹, A², A³ and A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   Z is Z⁶ selected from indolyl, indazolyl, benzimidazolyl,        pyrrolopyridinyl or triazolopyridinyl and is optionally        substituted by 1 or 2 substituents, which may be the same or        different, selected from R¹⁴, or is optionally substituted by 1        substituent selected from R¹⁵ and further optionally substituted        by 1 substituent selected from R¹⁴;    -   R¹⁴ represents fluoro, chloro, bromo, methyl, ethyl, formyl,        difluoromethyl, trifluoromethyl, cyanomethyl, methoxy, ethoxy,        methylcarbonyl, methoxycarbonyl, ethoxycarbonyl; and    -   R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl,        wherein phenoxy and phenylsulfanyl are optionally substituted by        1, 2 or 3 substituents, which may be the same or different,        selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and        ethoxy.

The compounds of the present invention may be enantiomers of thecompound of Formula (I) (when n=1) as represented by a Formula (Ia) or aFormula (Ib), wherein R⁵ and R⁶ are different substituents.

Likewise, the compounds of the present invention may be enantiomers(when n=2) when at one of the two carbon positions bound to R⁵ and R⁶,R⁵ and R⁶ are different substituents and at the other carbon position,R⁵ and R⁶ are the same. Alternatively, the compounds of Formula (I) maybe diastereomers (when n=2) when at each of the two carbon positionsbound to R⁵ and R⁶, R⁵ and R⁶ are different.

It is understood that when in aqueous media, the compounds of formula(I) according to the invention may be present in a reversibleequilibrium with the corresponding covalently hydrated forms (ie, thecompounds of formula (I-I) and formula (I-II) as shown below) at theCF₃-oxadiazole motif. This dynamic equilibrium may be important for thebiological activity of the compounds of Formula (I). The designations ofn, A¹, A², A³, A⁴, R¹, R², R³, R⁴, R⁵, R⁶, Z (Z¹, Z², Z³, Z⁴, Z⁵, Z⁶),R⁷, R⁸, R⁹, R¹⁰ (including R^(a), R^(b), R^(c), R^(d)), R¹¹ (includingR^(e), R^(f), R^(g), R^(h)), R¹², R¹³, R¹⁴, and R¹⁵ with reference tothe compounds of formula (I) of the present invention apply generally tothe compounds of Formula (I-I) and Formula (I-I), as well as to thespecific disclosures of combinations of n, A¹, A², A³, A⁴, R¹, R², R³,R⁴, R⁵, R⁶, Z (Z¹, Z², Z³, Z⁴, Z⁵, Z⁶), R⁷, R⁸, R⁹, R¹⁰ (includingR^(a), R^(b), R^(c), R^(d)), R¹¹ (including R^(e), R^(f), R^(g), R^(h)),R¹², R¹³, R¹⁴, and R¹⁵ as represented in Tables 1.1 to 1.12 (below) orthe compounds 1.1 to 1.312 according to the invention listed in Table T1(below).

Compounds of the present invention can be made as shown in the followingschemes 1 to 10, in which, unless otherwise stated, the definition ofeach variable is as defined above for a compound of formula (I).

Compounds of formula (I) can be prepared from compounds of formula (II),wherein X is a halogen, preferably Cl, Br or I, via treatment withcompounds of formula (III), in the presence of a base (e.g. K₂CO₃,Cs₂CO₃, or NaH) in a suitable solvent (e.g. dimethylformamide ortetrahydrofuran) at a temperature between 25° C. and 110° C. In somecases, a better reaction performance may be gained from the use of acatalyst (eg, NaI or 4-dimethylaminopyridine) and with microwaveirradiation. For related examples, see: WO 2013/132253 and Garcia, M. etal Org. Biomol. Chem. (2004), 11, 1633. This reaction is shown in Scheme1.

Additionally, compounds of formula (I), wherein preferably n is 1, canbe prepared from compounds of formula (IV) by treatment withtrifluoroacetic anhydride in the presence of a base (eg, pyridine or4-dimethylaminopyridine) in a suitable solvent, such as tetrahydrofuranor ethanol, at a temperature between 25° C. and 75° C. For relatedexamples, see WO 2003/028729 and WO 2010/045251. This reaction is shownin Scheme 2.

Compounds of formula (IV) can be prepared from compounds of formula (V)by treatment with a hydroxylamine hydrochloride salt in the presence ofa base, such as triethylamine, in a suitable solvent, such as methanol,at a temperature between 0° C. and 100° C. For related examples, seeKitamura, S. et al Chem. Pharm. Bull. (2001), 49, 268 and WO2013/066838. This reaction is shown in Scheme 3.

Compounds of formula (V) can be prepared from compounds of formula (VI),wherein Y is Br or I, via metal-promoted reaction with a suitablecyanide reagent, such as Pd(0)/Zn(CN)₂ or CuCN, in a suitable solvent(eg, dimethylformamide or N-methylpyrrolidone) at elevated temperaturebetween 100° C. and 120° C. For related examples, see US 2007/0155739and WO 2009/022746. This reaction is shown in Scheme 4.

Compounds of formula (VI), wherein preferably n is 1, can be preparedfrom compounds of formula (VII), wherein X is a halogen, preferably Cl,Br or I, via treatment with compounds of formula (III), in the presenceof a base (e.g. K₂CO₃, Cs₂CO₃, or NaH) in a suitable solvent (e.g.dimethylformamide or tetrahydrofuran) at a temperature between 25° C.and 110° C. In some cases, a better reaction performance may be gainedfrom the use of a catalyst (eg, NaI or 4-dimethylaminopyridine) and withmicrowave irradiation. For related examples, see: WO 2013/132253 andGarcia, M. et al Org. Biomol. Chem. (2004), 11, 1633. This reaction isshown in Scheme 5.

Compounds of formula (II), wherein n is 1 and X is Cl or Br, can beprepared from compounds of formula (VIII) by treatment with a halogensource (eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and aradical initiator (eg, (PhCO₂)₂ or azobisisobutyronitrile (AIBN)) in asuitable solvent, such as tetrachloromethane, at temperatures between55° and 100° C. in the presence of ultraviolet light. For relatedexamples, see Liu, S. et al Synthesis (2001), 14, 2078 and Kompella, A.et al Org. Proc. Res. Dev. (2012), 16, 1794. This reaction is shown inScheme 6.

Alternatively, compounds of formula (II) can be prepared from compoundsof formula (IX) by treatment with trifluoroacetic anhydride in thepresence of a base (eg, pyridine or 4-dimethylaminopyridine) in asuitable solvent, such as tetrahydrofuran or ethanol, at a temperaturebetween 25° C. and 75° C. For related examples, see WO 2003/028729 andWO 2010/045251. This reaction is shown in Scheme 7.

Compounds of formula (IX) can be prepared from compounds of formula (X)by treatment with a hydroxylamine hydrochloride salt in the presence ofa base, such as triethylamine, in a suitable solvent, such as methanol,at a temperature between 0° C. and 100° C. For related examples, seeKitamura, S. et al Chem. Pharm. Bull. (2001), 49, 268 and WO2013/066838. This reaction is shown in Scheme 8.

Compounds of formula (VII), wherein Y is Br, I or CN and X is Cl, Br orI, are either commercially available or can be prepared from compoundsof formula (XI), by treatment with a halogen source, (eg,N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radicalinitiator, such as (PhCO₂)₂ or azobisisobutyronitrile (AIBN), in thepresence of ultraviolet light, in a suitable solvent, such astetrachloromethane, at temperatures between 55° C. and 100° C. Forrelated examples, see Liu, S. et al Synthesis (2001), 14, 2078 andKompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794. This reactionis shown in Scheme 9.

Alternatively, compounds of formula (VII), wherein n is 1 and X is Cl,Br, I or OSO₂Me and Y is Br, I or CN, are either commercially availableor can be prepared from compounds of formula (XII), by treatment with ahalogen source (eg, CCl₃Br, CCl₄ or I₂) in the presence oftriphenylphosphine, or with methanesulfonyl chloride (CISO₂Me), in asuitable solvent, (eg, dichloromethane) at a temperature between 0° C.and 100° C. For related examples, see Liu, H. et al Bioorg. Med. Chem.(2008), 16, 10013, WO 2014/020350 and Kompella, A. et al Bioorg. Med.Chem. Lett. (2001), 1, 3161. Compounds of formula (XII) are commerciallyavailable. This reaction is shown in Scheme 10.

The compounds of formula (I) can be used in the agricultural sector andrelated fields of use, e.g., as active ingredients for controlling plantpests or on non-living materials for the control of spoilagemicroorganisms or organisms potentially harmful to man. The novelcompounds are distinguished by excellent activity at low rates ofapplication, by being well tolerated by plants and by beingenvironmentally safe. They have very useful curative, preventive andsystemic properties and can be used for protecting numerous cultivatedplants. The compounds of formula I can be used to inhibit or destroy thepests that occur on plants or parts of plants (fruit, blossoms, leaves,stems, tubers, roots) of different crops of useful plants, while at thesame time protecting also those parts of the plants that grow later,e.g., from phytopathogenic microorganisms.

The present invention further relates to a method for controlling orpreventing infestation of plants or plant propagation material and/orharvested food crops susceptible to microbial attack by treating plantsor plant propagation material and/or harvested food crops wherein aneffective amount a compound of formula (I) is applied to the plants, toparts thereof or the locus thereof.

It is also possible to use compounds of formula (I) as fungicide. Theterm “fungicide” as used herein means a compound that controls,modifies, or prevents the growth of fungi. The term “fungicidallyeffective amount” means the quantity of such a compound or combinationof such compounds that is capable of producing an effect on the growthof fungi. Controlling or modifying effects include all deviation fromnatural development, such as killing, retardation and the like, andprevention includes barrier or other defensive formation in or on aplant to prevent fungal infection.

It may also be possible to use compounds of formula (I) as dressingagents for the treatment of plant propagation material, e.g., seed, suchas fruits, tubers or grains, or plant cuttings, for the protectionagainst fungal infections as well as against phytopathogenic fungioccurring in the soil. The propagation material can be treated with acomposition comprising a compound of formula (I) before planting: seed,for example, can be dressed before being sown. The active compounds offormula (I) can also be applied to grains (coating), either byimpregnating the seeds in a liquid formulation or by coating them with asolid formulation. The composition can also be applied to the plantingsite when the propagation material is being planted, for example, to theseed furrow during sowing. The invention relates also to such methods oftreating plant propagation material and to the plant propagationmaterial so treated.

Furthermore, the compounds of formula (I) can be used for controllingfungi in related areas, for example in the protection of technicalmaterials, including wood and wood related technical products, in foodstorage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g. lumber, wall boards and paint.

The compounds of formula (I) are for example, effective against fungiand fungal vectors of disease as well as phytopathogenic bacteria andviruses. These fungi and fungal vectors of disease as well asphytopathogenic bacteria and viruses are for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp,Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A.niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechsleraspp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp.including E. cichoracearum, Eutypa lata, Fusarium spp. including F.culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum,F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp,Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis,Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp,Stagonospora nodorum, Stemphylium spp. Stereum hirsutum, Thanatephoruscucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp.including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp,Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturiaspp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

The compounds of formula (I) may be used for example on turf,ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens,for example conifers, as well as for tree injection, pest management andthe like.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The term “useful plants” is to be understood as also including usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” is to be understood as also including usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses aCryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses aCryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses aCryIA(b) and a CryIIIB(b1) toxin); Starlink® (maize variety thatexpresses a Cry9(c) toxin); Herculex I® (maize variety that expresses aCryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium);NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); BollgardI® (cotton variety that expresses a CryIA(c) toxin); Bollgard II®(cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin);VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potatovariety that expresses a CryIIIA toxin); NatureGard® Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11corn borer (CB) trait), Agrisure® RW (corn rootworm trait) andProtecta®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such asδ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

Further, in the context of the present invention there are to beunderstood by 6-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2,Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins(Vip), for example Vip1, Vip2, Vip3 or Vip3A, expressly also hybridtoxins, truncated toxins and modified toxins. Hybrid toxins are producedrecombinantly by a new combination of different domains of thoseproteins (see, for example, WO 02/15701). Truncated toxins, for examplea truncated Cry1Ab, are known. In the case of modified toxins, one ormore amino acids of the naturally occurring toxin are replaced. In suchamino acid replacements, preferably non-naturally present proteaserecognition sequences are inserted into the toxin, such as, for example,in the case of Cry3A055, a cathepsin-G-recognition sequence is insertedinto a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278,WO95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein CryIF for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There can be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants can be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

The compounds of formula I may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solidor liquid and are substances useful in formulation technology, e.g.natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

Suspension concentrates are aqueous formulations in which finely dividedsolid particles of the active compound are suspended. Such formulationsinclude anti-settling agents and dispersing agents and may furtherinclude a wetting agent to enhance activity as well an anti-foam and acrystal growth inhibitor. In use, these concentrates are diluted inwater and normally applied as a spray to the area to be treated. Theamount of active ingredient may range from 0.5% to 95% of theconcentrate.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other liquid carriers. The particlescontain the active ingredient retained in a solid matrix. Typical solidmatrices include fuller's earth, kaolin clays, silicas and other readilywet organic or inorganic solids. Wettable powders normally contain from5% to 95% of the active ingredient plus a small amount of wetting,dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles and are usually applied without dilution to the area in whichtreatment is required. Typical carriers for granular formulationsinclude sand, fuller's earth, attapulgite clay, bentonite clays,montmorillonite clay, vermiculite, perlite, calcium carbonate, brick,pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corncobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate,sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide,titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth,calcium sulphate and other organic or inorganic materials which absorbor which can be coated with the active compound. Granular formulationsnormally contain 5% to 25% of active ingredients which may includesurface-active agents such as heavy aromatic naphthas, kerosene andother petroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the activeingredient enclosed in an inert porous shell which allows escape of theenclosed material to the surroundings at controlled rates. Encapsulateddroplets are typically 1 to 50 microns in diameter. The enclosed liquidtypically constitutes 50 to 95% of the weight of the capsule and mayinclude solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimetre to1 centimetre and preferably 1 to 2 millimetres in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurisedsprayers, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporisation of a low boiling dispersant solventcarrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful informulating the compositions of the invention in the formulation typesdescribed above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water,toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethylketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone,amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol,alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine,p-diethylbenzene, diethylene glycol, diethylene glycol abietate,diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether,dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethylacetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane,2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycolbutyl ether, ethylene glycol methyl ether, gamma-butyrolactone,glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate,hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate,isooctane, isophorone, isopropyl benzene, isopropyl myristate, lacticacid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyloleate, methylene chloride, m-xylene, n-hexane, n-octylamine,octadecanoic acid, octyl amine acetate, oleic acid, oleylamine,o-xylene, phenol, polyethylene glycol (PEG400), propionic acid,propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene,triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin,mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, methanol, ethanol, isopropanol, and highermolecular weight alcohols such as amyl alcohol, tetrahydrofurfurylalcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol,glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrierof choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide,pyrophillite clay, silica, attapulgite clay, kieselguhr, chalk,diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller'searth, cotton seed hulls, wheat flour, soybean flour, pumice, woodflour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed inboth said liquid and solid compositions, especially those designed to bediluted with carrier before application. These agents, when used,normally comprise from 0.1% to 15% by weight of the formulation. Theycan be anionic, cationic, non-ionic or polymeric in character and can beemployed as emulsifying agents, wetting agents, suspending agents or forother purposes. Typical surface active agents include salts of alkylsulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C.sub. 18 ethoxylate;alcohol-alkylene oxide addition products, such as tridecylalcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate;alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride; polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includecrystallisation inhibitors, viscosity modifiers, suspending agents,spray droplet modifiers, pigments, antioxidants, foaming agents,anti-foaming agents, light-blocking agents, compatibilizing agents,antifoam agents, sequestering agents, neutralising agents and buffers,corrosion inhibitors, dyes, odorants, spreading agents, penetrationaids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients orcompositions may be combined with the compositions of the invention andused in the methods of the invention and applied simultaneously orsequentially with the compositions of the invention. When appliedsimultaneously, these further active ingredients may be formulatedtogether with the compositions of the invention or mixed in, forexample, the spray tank. These further biocidally active ingredients maybe fungicides, herbicides, insecticides, bactericides, acaricides,nematicides and/or plant growth regulators.

Pesticidal agents are referred to herein using their common name areknown, for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

In addition, the compositions of the invention may also be applied withone or more systemically acquired resistance inducers (“SAR” inducer).SAR inducers are known and described in, for example, U.S. Pat. No.6,919,298 and include, for example, salicylates and the commercial SARinducer acibenzolar-S-methyl.

The compounds of formula (I) are normally used in the form ofagrochemical compositions and can be applied to the crop area or plantto be treated, simultaneously or in succession with further compounds.These further compounds can be e.g. fertilizers or micronutrient donorsor other preparations, which influence the growth of plants. They canalso be selective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula (I) or of at least one preferred individual compound as definedherein, in free form or in agrochemically usable salt form, and at leastone of the above-mentioned adjuvants.

The invention therefore provides a composition, preferably a fungicidalcomposition, comprising at least one compound formula (I) anagriculturally acceptable carrier and optionally an adjuvant. Anagricultural acceptable carrier is for example a carrier that issuitable for agricultural use. Agricultural carriers are well known inthe art. Preferably said composition may comprise at least one or morepesticidally-active compounds, for example an additional fungicidalactive ingredient in addition to the compound of formula (I).

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include thefollowing: acycloamino acid fungicides, aliphatic nitrogen fungicides,amide fungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone,4-chloro-2-cyano-N,-dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N-(I-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate,methyl(E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine,bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol,bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole,bupirimate, buthiobate, butylamine calcium polysulfide, captafol,captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin,carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan,chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb,chloropicrin, chlorothalonil, chlorozolinate, chlozolinate, climbazole,clotrimazole, clozylacon, copper containing compounds such as copperacetate, copper carbonate, copper hydroxide, copper naphthenate, copperoleate, copper oxychloride, copper oxyquinolate, copper silicate, coppersulphate, copper tallate, copper zinc chromate and Bordeaux mixture,cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1,1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, 0,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)—N-benzyl-N ([methyl (methyl-thioethylideneamino-oxycarbonyl) amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone, fenaminosulf,fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan,fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph,fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram,fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet,formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin,guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene,hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen,hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate,imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb,ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb,isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil,isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, mandipropamid, maneb, mebenil,mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil,mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl,metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb,methfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate,metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax,milneb, moroxydine, myclobutanil, myclozolin, nabam, natamycin,neoasozin, nickel dimethyldithiocarbamate, nitrostyrene,nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercurycompounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxine-copper,oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate,penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad,phenamacril, phenazin oxide, phosdiphen, phosetyl-AI, phosphorus acids,phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D,polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine,propamocarb, propiconazole, propineb, propionic acid, proquinazid,prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid,pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos,pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone,pyroquilon, pyroxychlor, pyroxyfur, pyrrolnitrin, quaternary ammoniumcompounds, quinacetol, quinazamid, quinconazole, quinomethionate,quinoxyfen, quintozene, rabenzazole, santonin, sedaxane, silthiofam,simeconazole, sipconazole, sodium pentachlorophenate, solatenol,spiroxamine, streptomycin, sulphur, sultropen, tebuconazole, tebfloquin,tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole,thiadifluor, thicyofen, thifluzamide, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thioquinox, thiram, tiadinil,timibenconazole, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon,triadimenol, triamiphos, triarimol, triazbutil, triazoxide,tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforine,triflumizole, triticonazole, uniconazole, urbacide, validamycin,valifenalate, vapam, vinclozolin, zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO 96/15121 and also withanthelmintic active cyclic depsipeptides such as those described in WO96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO94/19334, EP 0 382 173, and EP 0 503 538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO 95/19363 or WO 04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following: Organophosphates: acephate, azamethiphos,azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos,chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton,demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon,dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos,etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion,flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos,isothioate, isoxathion, malathion, methacriphos, methamidophos,methidathion, methyl-parathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl,phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon,phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

Another aspect of invention is related to the use of a compound offormula (I) or of a preferred individual compound as defined herein, ofa composition comprising at least one compound of formula (I) or atleast one preferred individual compound as above-defined, or of afungicidal or insecticidal mixture comprising at least one compound offormula (I) or at least one preferred individual compound asabove-defined, in admixture with other fungicides or insecticides asdescribed above, for controlling or preventing infestation of plants,e.g. useful plants such as crop plants, propagation material thereof,e.g. seeds, harvested crops, e.g. harvested food crops, or non-livingmaterials by insects or by phytopathogenic microorganisms, preferablyfungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, e.g., useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.,harvested food crops, or of non-living materials by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of formula (I) or of a preferred individualcompound as above-defined as active ingredient to the plants, to partsof the plants or to the locus thereof, to the propagation materialthereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by phytopathogenicor spoilage microorganisms or organisms potentially harmful to man,especially fungal organisms, to such a level that an improvement isdemonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of formula (I),or an agrochemical composition which contains at least one of saidcompounds, is foliar application. The frequency of application and therate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of formula (I)can also penetrate the plant through the roots via the soil (systemicaction) by drenching the locus of the plant with a liquid formulation,or by applying the compounds in solid form to the soil, e.g. in granularform (soil application). In crops of water rice such granulates can beapplied to the flooded rice field. The compounds of formula I may alsobe applied to seeds (coating) by impregnating the seeds or tubers eitherwith a liquid formulation of the fungicide or coating them with a solidformulation.

A formulation, e.g. a composition containing the compound of formula(I), and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula (I), may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of formula I per kg of seed,preferably from 0.01 to 10 g per kg of seed are generally sufficient.

Suitably, a composition comprising a compound of formula (I) accordingto the present invention is applied either preventative, meaning priorto disease development or curative, meaning after disease development.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixingthe active ingredients with appropriate formulation inerts (diluents,solvents, fillers and optionally other formulating ingredients such assurfactants, biocides, anti-freeze, stickers, thickeners and compoundsthat provide adjuvancy effects). Also conventional slow releaseformulations may be employed where long lasting efficacy is intended.Particularly formulations to be applied in spraying forms, such as waterdispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like),wettable powders and granules, may contain surfactants such as wettingand dispersing agents and other compounds that provide adjuvancyeffects, e.g. the ondensation product of formaldehyde with naphthalenesulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkylsulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g. as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of formula (I) optionallytogether with other active agents, particularly microbiocides orconservatives or the like. Concentrated forms of compositions generallycontain in between about 2 and 80%, preferably between about 5 and 70%by weight of active agent. Application forms of formulation may forexample contain from 0.01 to 20% by weight, preferably from 0.01 to 5%by weight of active agent. Whereas commercial products will preferablybe formulated as concentrates, the end user will normally employ dilutedformulations.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

Table 1.1: This table discloses 206 specific compounds of the formula(T-1):

wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹, R², R³,R⁴, R⁵, and R⁶ are hydrogen, and Z is as defined below in Table 1.

Each of Tables 1.2 to 1.12 (which follow Table 1) make available 206individual compounds of the formula (T-1) in which A¹, A², A³, A⁴, R¹,R², R³, R⁴, R⁵, and R⁶ are as specifically defined in Tables 1.2 to1.12, which refer to Table 1 wherein Z is specifically defined.

TABLE 1 Compound no. Z 1.001 (3-pyridyl)triazol-1-yl 1.002(4-chlorophenyl)tetrazol-2-yl 1.003 (4-methoxyphenyl)triazol-1-yl 1.004[(5-chloro-3-methoxy-2-pyridyl)- oxymethyl]triazol-1-yl 1.005[1-(2,6-diethylphenyl)-5-methyl- pyrazol-4-yl]triazol-1-yl 1.006[1-triazol-4-yl]methyl acetate 1.007 1,2,4-triazol-1-yl 1.0081,2,4-triazol-1-yl-3-carbonitrile 1.009 1,2,4-triazol-2-yl-3-amine 1.0101,2,4-triazol-2-yl-3-carbonitrile 1.011 1,2,4-triazol-4-yl 1.0121,2,4-triazol-4yl-3-amine 1.013 1-[pyrrol-2-yl]ethanone 1.0141H-triazol-4-ylmethyl acetate 1.015 2-(4-pyridyl)benzimidazol-1-yl 1.0162-(trifluoromethyl)benzimidazol-1-yl 1.017 2,4-dimethylimidazol-1-yl1.018 2-bromoimidazol-1-yl 1.019 2-ethylbenzimidazol-1-yl 1.0202-isopropylimidazol-1-yl 1.021 2-methylimidazol-1-yl 1.0222-phenylimidazol-1-yl 1.023 3-(cyano)-1,2,4-triazol-1-yl 1.0243-(trifluoromethyl)-1,2,4-triazol-1-yl 1.0253-(trifluoromethyl)pyrazol-1-yl 1.026 3,4,5-trimethylpyrazol-1-yl 1.0273,5-bis(difluoromethyl)pyrazol-1-yl 1.0283,5-bis(trifluoromethyl)pyrazol-1-yl 1.029 3,5-dimethylpyrazol-1-yl1.030 3,5-ethylpyrazol-1-yl 1.031 3-[4-[[4-(1-ethyl-3-methyl-pyrazol-4-yl)triazol-1-yl 1.032 3-[4-[[4-(1-ethyl-5-methyl-pyrazol-4-yl)triazol-1-yl 1.033 3-benzylsulfanyl-1,2,4-triazol-1-yl 1.0343-benzylsulfanyl-1,2,4-triazol-4-yl 1.0353-bromo-5-methoxy-1,2,4-triazol-1-yl 1.036 3-chloropyrazol-1-yl 1.0373-ethylsulfanyl-1,2,4-triazol-1-yl 1.0383-propylsulfanyl-1,2,4-triazol-1-yl 1.039 4-(1-ethyl-3-methylpyrazol-4-yl)triazol-1-yl 1.040 4-(1-ethyl-5-methylpyrazol-4- yl)triazol-1-yl1.041 4-(2-pyridyl)triazol-1-yl 1.0424-(3-methylimidazol-4-yl)triazol-1-yl 1.0434-(3-methylimidazol-4-yl)triazol-1-yl 1.044 4-(3-pyridyl)triazol-1-yl1.045 4-(3-thienyl)triazol-1-yl 1.046 4-(4-fluorophenyl)triazol-1-yl1.047 4-(4-methoxyphenyl)triazol-1-yl 1.048 4-(ethoxymethyl)triazol-1-yl1.049 4-(phenoxymethyl)triazol-1-yl 1.050 4-(p-tolyl)triazol-1-yl 1.0514-(triazolo[4,5-b]pyridin-1-yl 1.052 4-(triazolo[4,5-b]pyridin-3-yl1.053 4-(triazolo[4,5-b]pyridin-4-yl 1.0544-(trifluoromethyl)imidazol-1-yl 1.055 4-(trifluoromethyl)pyrazol-1-yl1.056 4,5-dichloroimidazol-1-yl 1.057 4-[(5-chloro-3-methoxy-2-pyridyl)oxymethyl]triazol-1-yl 1.058 4-bromo-2-methyl-imidazol-1-yl1.059 4-bromoimidazol-1-yl 1.060 4-bromopyrazol-1-yl 1.0614-chlorobenzimidazol-1-yl 1.062 4-chlorophenyl)imidazol-1-yl 1.0634-chloropyrazol-1-yl 1.064 4-cyclopentyltriazol-1-yl 1.0654-cyclopropyltriazol-1-yl 1.066 4-fluorophenyl)imidazol-1-yl 1.0674-iodoimidazol-1-yl 1.068 4-iodopyrazol-1-yl 1.0694-isobutyltriazol-1-yl 1.070 4-methylimidazol-1-yl 1.0714-phenylimidazol-1-yl 1.072 4-phenyltriazol-1-yl 1.073 4-pyrazol-1-yl1.074 4-tert-butyltriazol-1-yl 1.075 4-trimethylsilyltriazol-1-yl 1.0765-(cyano)-1,2,4-triazol-1-yl 1.0775-(trifluoromethyl)-1,2,4-triazol-1-yl 1.078 5,5-dimethyl-4H-oxazol-2-yl1.079 5,6-dichlorobenzotriazol-1-yl 1.0805,6-dihydrocyclopenta[c]pyrrol-1- yl-4-one 1.0815-bromo-3-methoxy-1,2,4-triazol-1-yl 1.0825-chloro-3-(trifluoromethyl)-1,2,4- triazol-1-yl 1.0835-chlorobenzotriazol-2-yl 1.084 5-ethylsulfanyl-1,2,4-triazol-1-yl 1.0855-iodoimidazol-1-yl 1.086 5-methoxy-1,2,4-triazol-1-yl-3- amine 1.0875-methoxy-1,2,4-triazol-2-yl-3- amine 1.088 5-methoxyindol-1-yl 1.0895-methyl-3- (trifluoromethyl)pyrazol-1-yl 1.090 5-methylindol-1-yl 1.0915-methyl-pyrazol-1-yl-3- carbonitrile 1.092 5-methyl-pyrazol-1-yl-3-ol1.093 5-phenylimidazol-1-yl 1.094 5-phenyltriazol-1-yl 1.0955-propylsulfanyl-1,2,4-triazol-1-yl 1.0966-chloro-5-fluoro-benzimidazol-1-yl 1.097 6-chloroindol-1-yl 1.0986-fluoroindol-1-yl 1.099 6-methoxypyrid-3-yl 1.1007-chlorobenzimidazol-1-yl 1.101 benzotriazol-1-yl 1.102benzotriazol-2-yl 1.103 dimethyl imidazol-1-yl-4,5- dicarboxylate 1.104ethyl 2-[1-pyrazol-3-yl]pyridine-3- carboxylate 1.105 ethyl3-(difluoromethyl)-pyrazol-1-yl-4- carboxylate 1.106 ethyl3-(trifluoromethyl)-pyrazol-1-yl-4- carboxylate 1.107 ethyl4-phenyl-pyrazol-1-yl-3- carboxylate 1.108 ethyl5-(difluoromethyl)-pyrazol-1-yl-4- carboxylate 1.109 ethyl5-cyclopropyl-pyrazol-1-yl-3- carboxylate 1.110 ethyl5-cyclopropyl-pyrazol-2-yl-3- carboxylate 1.111 ethyl5-methyl-imidazol-3-yl-4- carboxylate 1.112 ethyl5-propyl-imidazol-3-yl-4- carboxylate 1.113 ethyl5-propyl-imidazol-4-yl-4- carboxylate 1.114 ethylpyrazl-1-yl-4-carboxylate 1.115 imidazo-1-yl-carbonitrile 1.116imidazol-1-yl 1.117 imidazol-1-yl-4,5-dicarbonitrile 1.118imidazol-1-yl-4-carbaldehyde 1.119 imidazol-3-yl-4-carbaldehyde 1.120indazol-1-yl 1.121 indazol-1-yl-3-carbonitrile 1.122 indazol-2-yl 1.123methyl 1,2,4-triazol-1-yl-3-carboxylate 1.124 methyl1,2,4-triazol-2-yl-3-carboxylate 1.125 methyl1,2,4-triazol-4-yl-3-carboxylate 1.126 methyl1H-1,2,4-triazole-3-carboxylate 1.127 methyl1H-1,2,4-triazole-5-carboxylate 1.128 methyl 2-methyl-pyrrole-1-yl-3-carboxylate 1.129 methyl 3-(methoxymethyl)-pyrazol-1-yl- 4-carboxylate1.130 methyl 3-cyclopropyl-pyrazol-4-yl-4- carboxylate 1.131 methyl3-imidazol-3-yl-4-carboxylate 1.132 methyl5-(methoxymethyl)-pyrazol-1-yl- 4-carboxylate 1.133 methyl5-cyclopropyl-pyrazol-1-yl-4- carboxylate″ 1.134 methylimidazol-1-yl-4-carboxylate 1.135 methyl indazol-1-yl-4-carboxylate1.136 methyl indazol-2-yl-4-carboxylate 1.137 methylindol-1-yl-4-carboxylate 1.138 methyl pyrazol-yl-e-4-carboxylate 1.139N-(2-methoxyethyl) pyrazol-1-yl 4- carboxamide 1.140N-(cyclopropylmethyl) pyrazol-4-yl-4- carboxamide 1.141N,N-dimethyl-1,2,4-triazol-1-yl-3-amine 1.142N,N-dimethyl-pyrazol-1-yl-4- carboxamide 1.143N-[1-methyl-1-(1H-triazol-4- yl)ethyl]benzamide 1.144N-2-[1-[imidazol-4-yl]ethyl] acetamide 1.145N-cyclopropyl-pyrazol-1-yl-4- carboxamide 1.146N-methyl-pyrazol-yl-4-carboxamide 1.147 N-prop-2-ynyl pyrazol-1-yl-4-carboxamide 1.148 pyrazol-1-yl 1.149 pyrazol-1-yl-3-carbaldehyde 1.150pyrazol-1-yl-4-carbonitrile 1.151 pyrazol-1-yl-4-carboxylic acid 1.152pyrrol-1-yl-2-carbaldehyde 1.153 pyrrol-1-yl-3-carbonitrile 1.154pyrrolo[2,3-b]pyridin-1-yl 1.155pyrrolo[3,2-b]pyridin-1-yl-2-carbonitrile 1.156pyrrolo[3,2-b]pyridin-4-yl-2-carbonitrile 1.157 tert-butylN-(1H-triazol-4- ylmethyl)carbamate 1.158 triazol-1-yl 1.159triazol-2-yl 1.160 triazolo[4,5-b]pyridin-2-yl 1.161trimethyl-triazol-4-yl silane 1.162 1,2,4-triazol-1-yl-3-carbonitrile1.163 N,N-diethyl-pyrazol-1-yl-4-carboxamide 1.164N-methoxy-N-methyl-pyrazol-1-yl-4- carboxamide 1.165morpholino-[pyrazol-4-yl]methanone 1.166 tert-butylpyrazol-1-yl-4-carboxylate 1.167 isopropyl pyrazol-1-yl-4-carboxylate1.168 propyl pyrazol-1-yl-4-carboxylate 1.169 2-(dimethylamino)ethylpyrazol-1-yl-4- carboxylate 1.170 N-methoxy-pyrazol-1-yl-4-carboxamide1.171 N-ethyl-pyrazol-1-yl-4-carboxamide 1.172pyrazol-1-yl-4-carboxamide 1.173 methyl triazol-1-yl-4-carboxylate 1.174triazol-1-yl-4-carboxylic acid 1.175 N-methyl-triazol-1-yl-4-carboxamide1.176 pyrazol-1-yl-4-carbaldehyde 1.177N-ethyl-1-triazol-1-yl-4-carboxamide 1.178N-methoxy-N-methyl-triazol-1-yl-4- carboxamide 1.179 ethyltriazol-1-yl-4-carboxylate 1.180 N-methoxy-triazol-1-yl-4-carboxamide1.181 isopropyl triazol-1 -yl-4-carboxylate 1.182 methyltriazol-3-yl-4-carboxylate 1.183 N,N-dimethyl-triazol-1-yl-4-carboxamide1.184 N-(4-methoxyphenyl)-triazol-1-yl-4- carboxamide 1.185N-(4-chlorophenyl)-triazol-1-yl-4- carboxamide 1.186N-(4-pyridyl)-triazol-1-yl-4-carboxamide 1.187N-methoxy-pyrazol-1-yl-4-methanimine 1.188N-ethoxy-pyrazol-1-yl-4-methanimine 1.189N-propoxy-pyrazol-1-yl-4-methaninnine 1.190 N-isopropoxy-pyrazol-1-yl-4-methanimine 1.191 N-benzyloxy-pyrazol-1-yl-4- methanimine 1.192N-prop-2-ynoxy-pyrazol-1-yl-4- methanimine 1.193N-methyl-triazol-3-yl-4-carboxamide 1.194N-methoxy-pyrrolidin-1-yl-3-imine 1.195 N-methoxy-piperidin-1-yl-4-imine1.196 5-methylsulfonyl-1,2,4-triazol-1-yl 1.1975-methylsulfinyl-1,2,4-triazol-1-yl 1.1983-methylsulfonyl-1,2,4-triazol-1-yl 1.1993-methylsulfinyl-1,2,4-triazol-1-yl 1.2005-methylsulfanyl-1,2,4-triazol-1-yl 1.2013-methylsulfanyl-1,2,4-triazol-1-yl 1.202 1-piperidin-1-yl 1.2034-morpholin-1-yl 1.204 4-thiomorpholin-1-yl 1.2054-methylsulfonyl-piperazin-1-yl 1.206 2,6-dimethyl-4-morpholin-1-ylTable 1.2: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R³, R⁴,R⁵, and R⁶ are hydrogen, R¹ is fluorine, and Z is as defined above inTable 1.Table 1.3: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R³, R⁴,R⁵, and R⁶ are hydrogen, R¹ is chlorine, and Z is as defined above inTable 1.Table 1.4: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R³, R⁴,R⁵, and R⁶ are hydrogen, R¹ is methyl, and Z is as defined above inTable 1.Table 1.5: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is N, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R³, R⁴, R⁵,and R⁶ are hydrogen, and Z is as defined above in Table 1.Table 1.6: This table discloses 206 specific compounds of formula (T-1)wherein, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹, R², R⁴,R⁵, and R⁶ are hydrogen, R³ is fluorine, and Z is as defined above inTable 1.Table 1.7: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R⁴, R⁵,R⁶, and R⁷ are hydrogen, R¹ and R³ are fluorine, and Z is as definedabove in Table 1.Table 1.8: This table discloses 206 specific compounds of formula (T-1)wherein, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R³, R⁴, R⁵,and R⁶ are hydrogen, R¹ and R² are fluorine, and Z is as defined abovein Table 1.Table 1.9: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹, R², R³R⁴, and R⁵ are hydrogen, R⁶ is methyl, and Z is as defined above inTable 1.Table 1.10: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R⁴ and R⁵are hydrogen, R³ is fluorine, R⁶ is methyl, and Z is as defined above inTable 1.Table 1.11: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹, R², R⁵and R⁶ are hydrogen, R³ and R⁴ are fluorine, and Z is as defined abovein Table 1.Table 1.12: This table discloses 206 specific compounds of formula (T-1)wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R², R³, R⁵and R⁶ are hydrogen, R¹ and R⁴ are fluorine, and Z is as defined abovein Table 1.

EXAMPLES

The Examples which follow serve to illustrate the invention. Thecompounds of the invention can be distinguished from known compounds byvirtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppmor 0.2 ppm.

Compounds of Formula (I) may possess any number of benefits including,inter alia, advantageous levels of biological activity for protectingplants against diseases that are caused by fungi or superior propertiesfor use as agrochemical active ingredients (for example, greaterbiological activity, an advantageous spectrum of activity, an increasedsafety profile (including improved crop tolerance), improvedphysico-chemical properties, or increased biodegradability).

Throughout this description, temperatures are given in degrees Celsius(° C.) and “mp.” means melting point. LC/MS means Liquid ChromatographyMass Spectrometry and the description of the apparatus and the method(Methods A, B and C) is as follows:

The description of the LC/MS apparatus and the method A is:SQ Detector 2 from WatersIonisation method: ElectrosprayPolarity: positive and negative ionsCapillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650 Mass range: 100 to 900 DaDAD Wavelength range (nm): 210 to 500Method Waters ACQUITY UPLC with the following HPLC gradient conditions:(Solvent A: Water/Methanol 20:1+0.05% formic acid and Solvent B:Acetonitrile+0.05% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.85 1.2 0 1000.85 1.5 0 100 0.85Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

The Description of the LC/MS Apparatus and the Method B is:

SQ Detector 2 from WatersIonisation method: ElectrosprayPolarity: positive ions

Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone GasFlow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700

Mass range: 140 to 800 DaDAD Wavelength range (nm): 210 to 400Method Waters ACQUITY UPLC with the following HPLC gradient conditions(Solvent A: Water/Methanol 9:1+0.1% formic acid and Solvent B:Acetonitrile+0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 1000.75 2.8 0 100 0.75 3.0 100 0 0.75Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.The description of the LC/MS apparatus and the method C is:SQ Detector 2 from WatersIonisation method: ElectrosprayACQUITY H Class UPLC, Mass Spectrometer from WatersPolarity: positive and Negative Polarity Switch

Scan Type MS1 Scan Capillary (kV) 3.00, Cone (V) 40.00, DesolvationTemperature (° C.) 500, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow(L/Hr) 1000

Mass range: 0 to 2000 DaDAD Wavelength range (nm): 200 to 350Method Waters ACQUITY UPLC with the following HPLC gradient conditions(Solvent A: Water +, 0.1% formic acid and Solvent B: Acetonitrile)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 70 30 0.5 0.05 70 30 0.50.8 5 95 0.5 1.8 5 95 0.5 2.45 70 30 0.5 2.50 70 30 0.5Type of column: Waters ACQUITY UPLC BEH C18; Column length: 50 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.7 micron;Temperature: 35° C.

Where necessary, enantiomerically pure final compounds may be obtainedfrom racemic materials as appropriate via standard physical separationtechniques, such as reverse phase chiral chromatography, or throughstereoselective synthetic techniques, eg, by using chiral startingmaterials.

FORMULATION EXAMPLES

Wettable powders a) b) c) active ingredient [compound of formula (I)]25%  50% 75% sodium lignosulfonate 5%  5% — sodium lauryl sulfate 3% — 5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethyleneglycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersedsilicic acid 5% 10% 10% Kaolin 62%  27% —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for dry seed treatment a) b) c) active ingredient [compound offormula (I)] 25% 50% 75% light mineral oil  5%  5%  5% highly dispersedsilicic acid  5%  5% — Kaolin 65% 40% — Talcum — 20%

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of formula (I)] 10%octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide)calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 molof ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4%Talcum 95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruder granules Active ingredient [compound of formula (I)] 15% sodiumlignosulfonate  2% Carboxymethylcellulose  1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated granules Active ingredient [compound of formula (I)] 8%polyethylene glycol (mol. wt. 200) 3% Kaolin 89% 

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension concentrate active ingredient [compound of formula (I)] 40%propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol ofethylene oxide)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1%silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Flowable concentrate for seed treatment active ingredient [compound offormula (I)] 40%  propylene glycol 5% copolymer butanol PO/EO 2%tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (inthe form of a 20% solution in 0.5%  water) monoazo-pigment calcium salt5% Silicone oil (in the form of a 75% emulsion in water) 0.2%  Water45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow-Release Capsule Suspension

28 parts of a combination of the compound of formula I are mixed with 2parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspensionin an apparatus suitable for that purpose.

List of Abbreviations

-   AIBN=azobisisobutyronitrile-   DMF=dimethylformamide-   DIPEA=N,N-di-isopropylethylamine-   EtOAc=ethyl acetate-   HCl=hydrochloric acid-   mp=melting point-   ° C.=degrees Celsius-   MeOH=methyl alcohol-   NaOH=sodium hydroxide-   NBS=N-bromosuccinimide-   min=minutes-   RT=room temperature-   h=hour(s)-   TFAA=trifluoroacetic acid anhydride-   THF=tetrahydrofuran-   t_(R)=retention time (in minutes)-   LC/MS=Liquid Chromatography Mass Spectrometry (description of the    apparatus and the methods used for LC/MS analysis are given above)

Example 1

This example illustrates the preparation3-[4-(imidazol-1-ylmethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(Compound 1.18 of Table T1)

Step 1: Preparation of N′-hydroxy-4-methyl-benzamidine

To a stirred suspension of 4-methylbenzonitrile (35 g, 0.29 mol) inethanol (220 mL) and water (440 mL) at RT was added hydroxylaminehydrochloride (41.1 g, 0.58 mol), potassium carbonate (65.4 g, 0.47 mol)and 8-hydroxyquinoline (0.22 g, 1.5 mmol). The reaction mixture washeated at 80° C. for 4 hours. The mixture was cooled to RT and dilutedwith 2N HCl until pH 8. Ethanol was evaporated under reduced pressure.The mixture was filtered, washed with water and dried under vacuum toafford the title compound. LC/MS (Method A) retention time=0.23 minutes,151.0 (M+H).

Step 2: Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirred solution of N′-hydroxy-4-methyl-benzamidine (38.7 g, 0.25mol) in 2-methyltetrahydrofuran (750 mL) was added TFAA at 0° C. Thereaction mixture was stirred at 15° C. for two hours and then dilutedwith water. The organic layer was separated, washed successively withsodium bicarbonate solution, ammonium chloride solution, water, driedover sodium sulfate, filtered and evaporated to dryness. The crudeproduct was subjected to flash chromatography over silica gel (750 gpre-packed column) with heptane/EtOAc 99:1 to 90:10 to afford the titlecompound as a clear oil, which solidified after storage.

LC/MS (Method A) retention time=1.15 minutes, mass not detected.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.41 (s).

Step 3a: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A stirred mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole(56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in tetrachloromethane (480mL) under argon was heated to 70° C. AIBN (4.03 g, 24 mmol) was addedand the reaction mixture stirred at 65° C. for 18 hours. The mixture wascooled to RT and diluted with dichloromethane and water and the layerswere separated. The organic layer was washed with sodium bicarbonatesolution, dried over sodium sulfate, filtered and evaporated to dryness.The crude residue was subjected to flash chromatography over silica gel(750 g pre-packed column) with cyclohexane/EtOAc 100:0 to 95:5 to affordthe title compound as a white solid mp: 58-63° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.32 (s).

3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole wasisolated as by-product as a white solid mp: 61-66° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.34 (s).

Step 3b: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole from3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirred 1:9 ratio mixture of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole and3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (10.2g) in acetonitrile (95 mL), water (1.9 mL) and DIPEA (6.20 ml, 35.7mmol) was added diethylphosphite (4.7 mL, 35.7 mmol) at 5° C. Themixture was stirred at 5-10° C. for two hours, water and 1M HCl wasadded and acetonitrile evaporated under reduced pressure. The whiteslurry was extracted three times with dichloromethane. The combinedorganic layers were dried over sodium sulfate, and filtered. The solventwas removed under reduced pressure and the resultant crude residuesubjected to flash chromatography over silica gel (40 g pre-packedcolumn) with cyclohexane/EtOAc 99:1 to 9:1 to afford3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.32 (s).

Step 4: Preparation of3-[4-(imidazol-1-ylmethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (100 mg,0.31 mmol), imidazole (1.5 equiv., 0.46 mmol), and potassium carbonate(2 equiv., 0.62 mmol) in acetonitrile (3.0 mL) was heated in a microwaveoven for 30 minutes at 120° C. Solids were removed by filtration andwashed with ethyl acetate and the mother liquors evaporated to give acrude residue. Further solvent was removed under reduced pressure andthe resultant residue purified by flash chromatography over silica gel(cyclohexane:EtOAc eluent gradient 1:0 to 0:1) to afford3-[4-(imidazol-1-ylmethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazoleas a yellow solid. LC/MS (Method A) retention time=0.69 minutes, 295(M+H). mp: 45-55° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.22 (d, 2H), 7.61 (d, 2H), 7.28 (d, 2H),7.14 (s, 1H), 5.20 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.39 (s).

Example 2

This example illustrates the preparation3-[4-[(4-cyclopentyltriazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(Compound 1.24 of Table T1)

A solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (153 mg,0.49 mmol) was dissolved in dimethylformamide (1.5 mL), isopropanol (1mL) and water (1 mL). To the resultant white suspension was introducedsodium azide (64 mg), copper (II) sulfate (28 mg), and copper cyanide(18 mg). To the fine beige suspension was introduced ethynylcyclopentane (0.06 mL) and triethylamine (1 mL) and the light green,cloudy solution was stirred over night at RT. The mixture was pouredinto a separatory funnel containing water and EtOAc, the layers wereseparated, and the aqueous fraction was then extracted with ethylacetate. The combined organics were dried over sodium sulfate andconcentrated under reduced pressure to afford the crude as a green oil.The crude was subject to combiflash chromatography over silicagel(heptane:EtOAc eluent gradient 99:1 to 1:1) to afford3-[4-[(4-cyclopentyltriazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazoleas a white solid. LC/MS (Method A) retention time=1.10 minutes, 364(M+H). mp: 117-119° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.12 (d, 2H), 7.39 (d, 2H), 7.22 (s, 1H),5.57 (s, 1H), 3.18 (m, 1H), 2.09 (m, 2H), 1.75 (m, 2H), 1.70 (m, 4H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.39 (s).

Example 3

This example illustrates the preparation of3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(Compound 1.42 of Table T1 below)

Step 1: Preparation of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride

4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid (4.00 g, 15.0mmol) was suspended in dichloromethane (90 mL) DMF (0.01 mL, 0.150 mmol)was added followed by oxalyl chloride (1.46 mL, 16.5 mmol). The mixturewas heated at reflux for 2 hours. The mixture was evaporated underreduced pressure to afford 4.15 g of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride as a yellowsolid.

Step 2: Preparation ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoylchloride from Step 1 (4.15 g, 14.6 mmol) in dichloromethane (20 mL) wasadded drop wise at room temperature to a stirred solution ofN-methoxymethanamine (1.10 g, 17.5 mmol) and triethylamine (3.10 ml,21.8 mmol) in dichloromethane (80 mL). The mixture was stirred at roomtemperature for 18 hours. The reaction mixture was poured into waterextracted twice with dichloromethane. The combined organic layers werewashed with brine, dried over sodium sulfate, and filtered. The solventwas removed under reduced pressure and the resultant crude residue wassubjected to flash chromatography over silica gel (heptane:EtOAc eluentgradient 9:1 to 65:35) to afford 4.12 g ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamideas a solid. LC/MS (Method A) retention time=0.97 minutes, 302 (M+H).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.18 (d, 2H), 7.84 (d, 2H), 3.56 (s, 3H),3.40 (s, 3H).

Step 3: Preparation of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

In a 75-mL multi neck flask equipped with stirrer, thermometer at −78°C. under argon, DIBAL-H, 1.0M in toluene (16 mL, 16.0 mmol) was addeddrop-wise to a solution ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(4.10 g, 13.3 mmol) in 2-methyltetrahydrofuran (90 mL). The mixture wasstirred two hours at −78° C. and for one hour temperature was letincrease to 0° C. Complete conversion observed by LC-MS. The mixture wasquenched by drop wise addition of sat. ammonium chloride solution.Precipitation of a white solid occurred. 4 M HCl was added until fullsolubilisation. The mixture was extracted thrice with ethyl acetate.Combined organics were dried over magnesium sulfate and evaporated toafford the crude as beige solid. The crude was subject to combiflashchromatography over silica gel (heptane:EtOAc eluent gradient 99:1 to90:10) to afford 2.93 g of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde as a whitesolid. mp: 40-50° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 10.12 (s, 1H), 8.31 (d, 2H), 8.05 (d,2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.29 (s).

Step 4: Preparation of1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol

In a 50 mL flask dried and under argon,4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (1.36 mol) wasdissolved in THF (10 mL) and cooled to −78° C. via a dry ice acetonebath. To this solution was introduced dropwise methyl magnesium bromide(0.70 mL, 2.03M in diethyl ether). The mixture was stirred for 1h at−78° C. and then was quenched with a saturated aqueous ammonium chloridesolution. The dry ice bath was removed, and the reaction was stirred atrt 5 min. it was then extracted with ethyl acetate. The combinedorganics were dried over sodium sulfate and concentrated under reducedpressure to afford the crude as a colourless oil. The crude was subjectto combiflash chromatography over silicagel (heptane:EtOAc eluentgradient 99:1 to 1:1) to afford1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol as a whitesolid.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.12 (d, 2H), 7.54 (d, 2H), 5.00 (s, 1H),1.54 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.31 (s).

Step 5: Preparation of1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone

In a 50 mL flask dried and under argon,1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (1.36 mol)was dissolved in dichloromethane (10 mL). To this solution wasintroduced manganese oxide (40.6 mmol) and the heterogenous mixture wasstirred for overnight at RT. The reaction solution was then filteredover a pad of celite and after washings with dichloromethane thecombined organics were concentrated under reduced pressure to affordcrude 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone asa white solid which was used directly without further purification.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.24 (d, 2H), 8.12 (d, 2H), 2.67 (s, 1H),1.56 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.39 (s).

Step 6: Preparation of4-methyl-N-[(E)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamide

In a 50 mL flask dried and under argon,1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone (1.05mol) was dissolved in methanol (10 mL). To this solution was introduced4-methylbenzenesulfonohydrazide (1.16 mmol) and the resultant whitesuspension was stirred for overnight at RT. The reaction solution wasthen concentrated under reduced pressure to afford crude4-methyl-N-[(E)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamideas a white solid which was used directly without further purification.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.12 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H),7.60 (s_(br), 1H), 7.36 (d, 2H), 2.44 (s, 3H), 2.17 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.34 (s).

Step 7: Preparation of3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

In a 10 mL flask dried and under argon,4-methyl-N-[(E)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamide(0.47 mol) was dissolved in dioxane (1.4 mL). To this solution wasintroduced 2-methoxypyridine boronic acid (0.71 mmol) and the resultantbeige suspension was stirred for 3h at 110° C. After cooling to RT, thereaction solution was then concentrated under reduced pressure and thecrude was subject to combiflash chromatography over silicagel(cyclohexane:EtOAc eluent gradient 99:1 to 4:1) to afford3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazoleas a yellow oil.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.07 (d, 1H), 8.03 (d, 2H), 7.38 (d, 1H),7.36 (d, 2H), 6.69 (d, 1H), 4.18 (q, 1H), 3.92 (s, 3H), 1.67 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.38 (s).

Example 4

This example illustrates the preparation of3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(Compound 1.303 of Table T1 below).

Step 1: Preparation of3-[4-(1-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a solution of1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (1.15 g,4.45 mmol) in dichloromethane (15 mL) cooled to 0° C. using an ice bathwas added tribromophosphane (0.465 ml, 4.90 mmol) over 30 minutes andthe reaction mixture was stirred for 1.5 hrs. Then, an ice bath was usedto cool the contents and a 10% sodium metabisulphite (50 ml) wasintroduced. After 15 minutes, the aqueous layer was extracted withdichloromethane and the total combined organic layer was washed withwater and dried over Na₂SO₄, filtered and concentrated under reducedpressure. The resultant crude residue was purified by combiflashchromatography over silica gel using cyclohexane as eluent to affordpure 3-[4-(1-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1g, 71% yield) as white solid.

¹H NMR (400 MHz, DMSO-d6) δ ppm: 8.07 (m, 2H), 7.75 (m, 2H), 5.76 (s,1H), 5.59 (q, 1H), 2.02 (d, 3H).

Step 2: Preparation of3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

3-[4-(1-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (150 mg,0.47 mmol), 3,5-dimethylpyrazole (0.07 g, 0.70 mmol) and potassiumcarbonate (0.130 g, 0.93 mmol) were dissolved in acetonitrile (5 mL) ina microwave vial. The mixture was then heated in the microwave at 100°C. for 30 minutes. The reaction mixture was diluted with water (20 mL)and extracted with ethyl acetate. The total combined organic layer waswashed with brine solution, dried over anhydrous Na₂SO₄, filtered, andconcentrated at reduced pressure. The resultant crude residue waspurified by combiflash chromatography over silica gel (cyclohexane:EtOAceluent gradient 92:8) to afford pure3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(55 mg, 35%) as a light yellow gummy mass. LC/MS (Method C) retentiontime=1.61 minutes, 337 (M+H).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.04 (d, 2H), 7.25 (m, 2H), 5.87 (s, 1H),5.41 (q, 1H), 2.30 (s, 3H), 2.12 (s, 3H), 1.95 (d, 3H).

Example 5

This example illustrates the preparation of3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(Compound 1.309 of Table T1 below).

Step 1 Preparation of3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1.2.4-oxadiazole

To a solution of 4-(2-bromoethyl)benzonitrile (2.0 g, 9.5 mmol) inethanol (32 mL) was added hydroxylamine hydrochloride (2 equiv., 19mmol) followed by triethylamine (4.5 equiv., 43 mmol). The reactioncontents were allowed to stir at ambient temperature for 12 hrs and thevolatiles were then removed at reduced pressure. The resultant crudemass was dissolved in tetrahydrofuran (60 mL), cooled to 00° C. using anice bath and trifluoroacetic anhydride (3 equiv., 29 mmol) was slowlyintroduced followed by the dropwise addition of pyridine (4 equiv., 38mmol) at 0° C. After warming to 25° C. and stirring for 5 hours thereaction mixture was diluted with water (100 mL) and extracted withethyl acetate. The combined total organic layer was washed with 1N HCland brine solution. The organic layer thus obtained was dried overanhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. Theresultant crude residue was purified by flash chromatography over silicagel using 30% ethyl acetate in hexane as eluent to afford pure3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.75 g,57% yield) as colourless gummy mass.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.09 (d, 2H), 7.39 (d, 2H), 3.62 (t, 2H),3.26 (t, 2H).

Step 2: Preparation of3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

3-[4-(2-Bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.150g, 0.467 mmol), 3,5-dimethyl-1H-pyrazole (1.5 equiv., 0.701 mmol) andpotassium carbonate (0.30 g, 0.934 mmol) were dissolved in acetonitrile(5 mL) in a microwave vial and the mixture was heated in the presence ofmicrowaves irradiation for 30 min at 100° C. Then the reaction mixturewas diluted with water (20 mL) and extracted with ethyl acetate. Thetotal combined organic layer was washed with water and brine solution.The organic layer thus obtained was dried over anhydrous Na₂SO₄,filtered, and concentrated under reduced pressure. The resultant cruderesidue was purified by flash chromatography over silica gel using 30%ethyl acetate in hexane as eluent to afford pure3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(0.03 g, 16% yield) as a colorless gummy mass. LC/MS (Method C)retention time=1.67 minutes, 337 (M+H).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.03 (m, 2H), 7.19 (m, 2H), 5.73 (s, 1H),4.21 (t, 2H), 3.21 (t, 2H), 2.28 (s, 3H), 1.88 (s, 3H).

Example 6

This example illustrates the preparation of ethyl1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-yl]phenyl]ethyl]pyrazole-4-carboxylate(Compound 1.310 of Table T1 below).

3-[4-(2-Bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.150g, 0.467 mmol) and ethyl 1H-pyrazole-4-carboxylate (0.03 g, 0.08 mmol)were suspended in acetonitrile (1 mL) and potassium carbonate (0.30 g,0.934 mmol) was introduced and the mixture was stirred for 16 hours.Then the reaction mixture was diluted with water (20 mL) and extractedwith ethyl acetate. The total combined organic layer was washed withwater and brine solution. The organic layer thus obtained was dried overanhydrous Na₂SO₄, filtered and concentrated under reduced pressure. Theresultant crude residue was purified by flash chromatography over silicagel using 30% ethyl acetate in hexane as eluent to afford pure ethyl1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]pyrazole-4-carboxylate(0.03 g, 20% yield) as a white solid. MP: 108-110° C. LC/MS (Method C)retention time=1.57 minutes, 381 (M+H).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.05 (m, 2H), 7.96 (s, 1H), 7.69 (s, 1H),7.23 (m, 2H), 4.41 (t, 2H), 4.28 (q, 2H) 3.30 (t, 2H), 1.33 (m, 3H).

The following general procedure was performed in a combinatorial fashionusing appropriate building blocks (compounds of Formulae (II) and (Ill))to provide the compounds of Formula (I). The compounds prepared via thefollowing combinatorial protocol were analyzed using LC/MS Method B.

By way of exemplification,3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.03mmol in 1000 μL acetonitrile) were transferred to microwave vialscontaining amine derivative of formula (II) (0.03 mmol), potassiumcarbonate (0.06 mmol), and were stirred under microwaves irradiation at120° C. for 20 minutes in the parallel microwave apparatus. The solventwas removed under a stream of nitrogen. The resultant crude residueswere solubilized in a mixture of MeOH (250 μL) and DMA (500 μL) anddirectly submitted for preparative LC/MS purification which provided thecompounds of formula (I). Structures of Isomers were assigned by NMRtechniques.

TABLE T1 Melting point (mp) and/or LC/MS data (retention time (t_(R)))for compounds of Formula (I): Mass t_(R) charge LCMS mp Entry Compoundname Structure (min) [M + H]⁺ Method (° C.) 1.1 3-[4-[[4-(1-ethyl-3-methyl-pyrazol-4- yl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

116.2- 118.2 1.2 3-[4-[[4-(1-ethyl-5- methyl-pyrazol-4- yl)triazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

138.3- 140.1 1.3 3-[4-[(5- phenyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.08 272.3 A 1.4 3-[4-[(4- phenyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

161.5- 164.4 1.5 3-[4-[(4- cyclopropyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

115.5- 117.2 1.6 3-[4-[[4-(3- methylimidazol-4- yl)triazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

108.7- 110.3 1.7 [1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazol-4-yl]methyl acetate

157.4- 160.4 1.8 3-[4-[[4-(3- thienyl)triazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

160.2- 163.9 1.9 tert-butyl N-[[1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazol-4- yl]methyl]carbamate

134.7- 136.9 1.10 3-[4-[(5,5-dimethyl- 4H-oxazol-2- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.71 326.2 A 1.11 3-[4-[[4- (ethoxymethyl)triazol- 1-yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

115.7- 117.6 1.12 3-[4-[[4-(4- methoxyphenyl) triazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

187.7- 196.2 1.13 3-[4-[[4-(4- fluorophenyl)triazol-1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

185.3- 189 1.14 3-[4-[[4-(p- tolyl)triazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

200.6- 204.2 1.15 3-[4-[(3,5- dimethylpyrazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

53- 58 1.16 3-[4-(pyrazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

36- 41 1.17 3-[4-[[3,5- bis(difluoromethyl) pyrazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

53- 58 1.18 3-[4-(imidazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

45- 55 1.19 3-[4-(1,2,4-triazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.30 296.1 B 72- 77 1.20 3-[4-[[5-methyl-3- (trifluoromethyl) pyrazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.17 377.4 A 1.21 5-(trifluoromethyl)-3- [4-[[3- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole

1.14 363.2 A 1.22 3-[4-[[4-(2- pyridyl)triazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

160.2- 162.4 1.23 3-[4-[[4-(3- pyridyl)triazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

159.8- 163.1 1.24 3-[4-[(4- cyclopentyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

117.9- 118.8 1.25 trimethyl-[1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazol-4-yl]silane

87.8- 89.5 1.26 3-[4-[(4- isobutyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

113.9- 115.7 1.27 3-[4-[(4-tert- butyltriazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

90.4- 92.3 1.28 3-[4-[[4- (phenoxymethyl) triazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

103.2- 104.9 1.29 3-[4-[[4-[(5-chloro-3- methoxy-2- pyridyl)oxymethyl]triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-

109.9- 113.3 1,2,4-oxadiazole 1.30 N-[1-methyl-1-[1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] triazol-4-yl]ethyl]benzamide

157.6- 161.9 1.31 3-[4-[[4-[1-(2,6- diethylphenyl)-5- methyl-pyrazol-4-yl]triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

157.6- 161.9 1.32 3-[4-(triazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.33 296.1 B 107.6- 109.5 1.33 3-[4-(triazol-2- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

105.4- 107.9 1.34 3-[4-(benzotriazol-2- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.85 346.1 B 112.4- 116.6 1.35 3-[4-(benzotriazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.67 346.1 B 142.3- 143.2 1.36 methyl 2-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3-

1.50 354.1 B 122.8- 124.4 carboxylate 1.37 methyl 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-1,2,4-triazole-3- carboxylate

1.35 354.1 B 174- 177.2 1.38 5-(trifluoromethyl)-3- [4-[[5-(trifluoromethyl)- 1,2,4-triazol-1- yl]methyl]phenyl]-

1.09 405.2 A 1,2,4-oxadiazole 1.39 5-(trifluoromethyl)-3-(trifluoromethyl)- 1,2,4-triazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole

1.69 364.1 B 68.2- 70.1 1.40 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile

1.56 321.1 B 1.41 2-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile

120- 124 1.42 3-[4-[1-(6-methoxy- 3- pyridyl)ethyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.26 350 A 1.43 dimethyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4,5- dicarboxylate

1.48 411.2 B 1.44 3-[4-[(4-iodopyrazol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.83 421.1 B 1.45 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4,5- dicarbonitrile

1.59 345.2 B 1.46 3-[4-[(4,5- dichloroimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.76 363.1 B 1.47 3-[4-[(2- phenylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.14 371.2 B 1.48 5-(trifluoromethyl)-3- [4-[[2- (trifluoromethyl)benzimidazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole

1.93 413.2 B 1.49 3-[4-[(2- bromoimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.54 373.1 B 1.50 1-[1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] indol-3-yl]ethanone

1.80 386.2 B 1.51 6-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indole-3-carbaldehyde

1.85 386.2 B 1.52 3-[4-[(5-methylindol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.05 358.2 B 1.53 3-[4-[(2- methylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.91 309.2 B 1.54 3-[4-[(6-fluoroindol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.05 362.2 B 1.55 5-(trifluoromethyl)-3- [4-[[4- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole

1.84 363.2 B 1.56 3-[4-[(2- isopropylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.03 337.2 B 1.57 5-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indole-3-carbaldehyde

1.75 402.2 B 1.58 2-[1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] benzimidazol-2- yl]acetonitrile

1.61 384.2 B 1.59 1-[1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrol-2-yl]ethanone

1.80 336.2 B 1.60 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrole-3-carbonitrile

1.70 319.2 B 1.61 ethyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4-carboxylate

1.71 367.2 B 120- 130 1.62 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrrole-2-carbaldehyde

1.73 322.2 B 1.63 3-[4-[(2- ethylbenzimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.24 373.2 B 1.64 3-[4-[(6-chloroindol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.14 378.2 B 1.65 3-[4-[[2-(4- fluorophenyl)imidazol-1-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.18 389.2 B 1.66 methyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] indole-4-carboxylate

1.98 402.2 B 1.67 3-[4-[(4- chloropyrazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.77 329.2 B 1.68 methyl 2-methyl-5- (trifluoromethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrole-3-carboxylate

1.96 434.4 B 1.69 3-[4-[(2,4,5- tribromoimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.98 528.5 B 1.70 2-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indole-3-carbaldehyde

1.81 386.2 B 1.71 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-2- carbaldehyde

1.46 323.2 B 1.72 3-[4-[(2-bromo-4,5- dichloro-imidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.97 441.0 B 1.73 3-[4-[[2-(4- pyridyl)benzimidazol-1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.59 422.3 B 1.74 2-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- 5,6- dihydrocyclopenta[c] pyrrol-4-one

1.61 348.2 B 1.75 3-[4-[(5- methoxyindol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.91 374.2 B 1.76 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4-carbonitrile

1.57 320.2 B 1.77 3-[4-[(4- bromopyrazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.80 373.1 B 1.78 3-[4-[(2,4- dimethylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.92 323.1 B 1.79 3-[4-[(4- bromoimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.55 373.0 B 1.80 ethyl 5-methyl-3-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4- carboxylate

1.47 381.2 B 1.81 1,3-dimethyl-7-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] purine-2,6-dione

1.43 407.2 B 1.82 3-[4-[(4- phenylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.26 371.2 B 1.83 3-[4-[(4- methylimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.88 309.1 B 1.84 ethyl 4-phenyl-1-[[4- [5-(trifluoromethyl)1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carboxylate

1.92 443.2 B 1.85 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-3- carbaldehyde

1.53 323.1 B 1.86 3-[4-(indazol-2- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.73 345.1 B 1.87 3-[4-(indazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.86 345.2 B 1.88 methyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4- carboxylate

1.34 353.1 B 1.89 methyl 3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4- carboxylate

1.42 353.1 B 1.90 5-(trifluoromethyl)-3- (trifluoromethyl) imidazol-1-yl]methyl]phenyl]- 1,2,4-oxadiazole

1.63 363.1 B 1.91 3-[4-[(4-bromo-2- methyl-imidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.53 387.0 B 1.92 3-[4-[(6-chloro-5- fluoro-benzimidazol-1-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.53 387.0 B 1.93 5-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carbonitrile

1.74 397.1 B 1.94 3-[4-[(4- chlorobenzimidazol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.71 334.1 B 1.95 3-[4-[(7- chlorobenzimidazol- 1-yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.67 379.1 B 1.96 3-[4-[(4- iodoimidazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.52 421.0 B 1.97 3-[3-methoxy-4- (1,2,4-triazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.38 325.1 B 102- 106 1.98 3-[4-(1,2,4-triazol-1- ylmethyl)-3-(trifluoromethyl) phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.53 363.1 B 1.99 3-[3-chloro-4-(1,2,4- triazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.44 329.0 B 63- 71 1.100 3-[3-chloro-4-[(3,5- dimethylpyrazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.89 356.1 B 1.101 3-[3-fluoro-4-(1,2,4- triazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.35 313.1 B 52- 63 1.102 3-[4-[(3,5- dimethylpyrazol-1-yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.89 356.1 B 50- 56 1.103 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-(trifluoromethyl) phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.99 440.0 B 1.104 dimethyl 1-[[2- chloro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4,5- dicarboxylate

1.60 444.0 B 1.105 3-[3-chloro-4-[(2,4- dimethylimidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.02 356.1 B 1.106 1-[[2-chloro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4,5- dicarbonitrile

1.69 378.0 B 1.107 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-chloro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.69 405.9 B 1.108 methyl 1-[[2-chloro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate

1.48 387.0 B 1.109 3-[3-chloro-4-[(4- methylimidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

0.99 342.0 B 1.110 3-[4-(benzimidazol- 1-ylmethyl)-3-chloro- phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.46 378.0 B 1.111 3-[3-chloro-4-[(4- chloropyrazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.91 362.0 B 1.112 3-[3-chloro-4- (imidazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.93 328.0 B 1.113 3-[3-chloro-4-[[5-(4- chlorophenyl)tetrazol-1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.92 440.0 B 1.114 3-[3-chloro-4-[(4- iodopyrazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.97 453.9 B 1.115 3-[4-[(4- bromopyrazol-1- yl)methyl]-3-chloro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.94 405.9 B 1.116 3-[4-[(5- bromoimidazol-1- yl)methyl]-3-methoxy-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.38 402.0 B 1.117 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-methoxy-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.62 402.0 B 1.118 dimethyl 1-[[2-fluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4,5- dicarboxylate

1.52 428.1 B 1.119 1-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4,5- dicarbonitrile

1.62 362.1 B 1.120 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.60 390.0 B 1.121 3-[4-[(4,5- dichloroimidazol-1- yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.80 380.0 B 1.122 methyl 1-[[2-fluoro-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate

1.40 371.1 B 1.123 3-[3-fluoro-4-[(2- methylimidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

0.93 326.1 B 1.124 3-[3-fluoro-4-[(4- methylimidazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

0.95 326.1 B 1.125 3-[3-fluoro-4- (pyrrolo[2,3- b]pyridin-7-ylmethyl)phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

0.97 362.1 B 1.126 3-[4-(benzimidazol- 1-ylmethyl)-3-fluoro- phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.33 362.1 B 1.127 3-[4-[(4-chloro-3,5- dimethyl-pyrazol-1-yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.99 374.1 B 1.128 3-[4-[(4- chloropyrazol-1- yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.82 346.0 B 1.129 3-[3-fluoro-4- (imidazol-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.89 312.1 B 1.130 3-[4-[[5-(4- chlorophenyl)tetrazol- 1-yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.84 424.0 B 1.131 3-[3-fluoro-4-[(4- iodopyrazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.87 438.0 B 1.132 3-[4-[(4- bromopyrazol-1- yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.84 390.0 B 1.133 dimethyl 1-[[5-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-2-pyridyl] methyl]imidazole- 4,5-dicarboxylate

1.30 411.1 B 1.134 3-[6-[(2,4- dimethylimidazol-1-yl)methyl]-3-pyridyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

0.83 323.1 B 1.135 1-[[5-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]-2- pyridyl]methyl] imidazole-4,5- dicarbonitrile

1.44 345.1 B 1.136 3-[6-[(4- bromoimidazol-1- yl)methyl]-3-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.74 397.1 B 1.137 3-[6-[(4,5- dichloroimidazol-1-yl)methyl]-3-pyridyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.56 363.0 B 1.138 methyl 1-[[5-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-2-pyridyl]methyl]- 1,2,4-triazole-3- carboxylate

1.16 354.1 B 1.139 3-[6-[(2- methylimidazol-1- yl)methyl]-3-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.77 309.1 B 1.140 3-[6-[(3,5- dimethylpyrazol-1- yl)methyl]-3-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.49 323.1 B 1.141 3-[6-(imidazol-1- ylmethyl)-3-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.72 295.1 B 1.142 3-[6-[[5-(4- chlorophenyl)tetrazol- 2-yl]methyl]-3-pyridyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.89 407.1 B 1.143 3-[6-(1,2,4-triazol-1- ylmethyl)-3-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.06 296.1 B 1.144 3-[6-[(4-iodopyrazol- 1-yl)methyl]-3- pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.56 373.0 B 1.145 3-[4-[(2,4- dimethylimidazol-1- yl)methyl]-3-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.01 340.1 B 1.146 5-(trifluoromethyl)-3- [4-[(3,4,5-trimethylpyrazol-1- yl)methyl]phenyl]- 1,2,4-oxadiazole

B 99.4- 102 1.147 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4-carboxylic acid

0.83 323.1 B 182- 192 1.148 N-cyclopropyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

1.44 345.1 B 189- 194 1.149 N,N-dimethyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

124- 129 1.150 N-methyl-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4- carboxamide

156- 161 1.151 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4- carbaldehyde

1.26 323.1 B 1.152 3-[4-[[5-(2- bromophenyl)tetrazol-1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.77 451.1 B 1.153 3-[4-[[5-(2- bromophenyl)tetrazol-2-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.98 451.1 B 1.154 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazole-4- carbonitrile

1.41 320.1 B 1.155 3-[4-[(5,6- dichlorobenzotriazol-1-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.98 414.1 B 1.156 N-[2-[1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] imidazol-4- yl]ethyl]acetamide

0.86 380.2 B 1.157 4-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrolo[3,2-b]pyridine- 2-carbonitrile

1.02 370.1 B 1.158 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrolo[3,2-b]pyridine- 2-carbonitrile

1.58 370.1 B 1.159 3-[4-[[6-(4- bromophenyl)sulfanyl- 5-chloro-benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.31 566.0 B 1.160 3-[4-[[5-(4- bromophenyl)sulfanyl- 6-chloro-benzotriazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.46 566.0 B 1.161 ethyl 5-(4- chlorophenyl)-2- (trifluoromethyl)-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]imidazole-4- carboxylate

2.08 545.2 B 1.162 ethyl 5-(4- chlorophenyl)-2- (trifluoromethyl)-3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]imidazole-4- carboxylate

2.27 545.2 B 1.163 3-[4-[[5-chloro-6-(4- methoxyphenoxy) benzotriazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.06 502.2 B 1.164 3-[4-[[5-chloro-6-(4- methoxyphenoxy) benzotriazol-2-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.21 502.2 B 1.165 3-[4-[[5-(4- fluorophenyl)-3- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.14 457.2 B 1.166 3-[4-[[3-(4- fluorophenyl)-5- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.25 457.2 B 1.167 3-[4-[[5-(2,4- difluorophenyl)-3- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.14 475.2 B 1.168 3-[4-[[3-(2,4- difluorophenyl)-5- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.31 475.2 B 1.169 methyl 5-(2,5- difluorophenyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-3-carboxylate

1.89 465.2 B 1.170 methyl 5-(2,5- difluorophenyl)-2-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-3-carboxylate

2.22 465.2 B 1.171 5-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-3-ol

1.40 325.1 B 1.172 3-[4-[[5-(4- methoxyphenyl)-3- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.14 469.2 B 1.173 3-[4-[[3-(4- methoxyphenyl)-5- (trifluoromethyl)pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.22 469.2 B 1.174 3-[4-[[4-(4- chlorophenyl)-2- (difluoromethyl-sulfanyl)imidazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

2.08 487.1 B 1.175 3-[4-[(6-bromo-4,5- dimethyl- benzotriazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.08 452.1 B 1.176 3-[4-[(6-bromo-4,5- dimethyl- benzotriazol-2-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.27 452.1 B 1.177 3-[4-[[6-(1,3- benzodioxol-5- yloxy)-5-chloro-benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.03 516.2 B 1.178 3-[4-[[5-(1,3- benzodioxol-5- yloxy)-6-chloro-benzotriazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.19 516.1 B 1.179 3-[4-[[4-chloro-5-(4- fluorophenoxy) benzotriazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.03 490.1 B 1.180 3-[4-[[7-chloro-6-(4- fluorophenoxy) benzotriazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.12 490.2 B 1.181 3-[4-[[4-chloro-5-(4- fluorophenoxy) benzotriazol-2-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.19 490.1 B 1.182 ethyl 5-(4- chlorophenyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-2-(trifluoromethyl- sulfanyl)imidazole-4- carboxylate

2.13 577.1 B 1.183 ethyl 5-(4- chlorophenyl)-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-2-(trifluoromethyl- sulfanyl)imidazole-4- carboxylate

2.30 577.1 B 1.184 ethyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] benzotriazole-5- carboxylate

1.84 418.2 B 1.185 ethyl 2-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] benzotriazole-5- carboxylate

2.00 418.2 B 1.186 ethyl 5-cyclopropyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carboxylate

1.87 407.2 B 1.187 ethyl 5-cyclopropyl- 2-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carboxylate

2.08 407.2 B 1.188 ethyl 5-phenyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4- carboxylate

1.72 443.2 B 1.189 ethyl 5-phenyl-3-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4- carboxylate

1.83 443.2 B 1.190 3-[4-[[2-methyl-6- (trifluoromethyl) benzimidazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.69 427.2 B 1.191 3-[4-[[2-methyl-5- (trifluoromethyl) benzimidazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.73 427.2 B 1.192 methyl 2-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indazole-4-carboxylate

1.80 403.2 B 1.193 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indazole-4-carboxylate

1.87 403.2 B 1.194 6-fluoro-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] indazole-3-carbonitrile

1.94 388.1 B 1.195 3-[4-[[4-chloro-6- (trifluoromethyl) benzotriazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.03 448.1 B 1.196 3-[4-[[7-chloro-5- (trifluoromethyl) benzotriazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.09 448.1 B 1.197 3-[4-[[4-chloro-6- (trifluoromethyl) benzotriazol-2yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

0.00 448.1 B 1.198 3-[4-[(4,5- dimethylbenzotriazol-1-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.88 374.2 B 1.199 3-[4-[(4,5- dimethylbenzotriazol-2-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

2.06 374.2 B 1.200 5-(trifluoromethyl)-2- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine

1.56 379.1 B 1.201 3-[4-[[5-(p- tolyl)tetrazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.78 387.2 B 1.202 3-[4-[[5-(p- tolyl)tetrazol-2- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.03 387.2 B 1.203 N,N-dimethyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine

1.44 339.2 B 1.204 ethyl 3- (difluoromethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate

1.82 417.2 B 1.205 ethyl 5- (difluoromethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate

1.97 417.2 B 1.206 3-[4-[(3- propylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.76 370.1 B 1.207 3-[4-[(5- propylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.82 370.1 B 1.208 3-[4-[(3- ethylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.64 356.1 B 1.209 3-[4-[(5- ethylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.70 356.1 B 1.210 4-chloro-5-(4- chlorophenyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-3-carbonitrile

2.18 464.1 B 1.211 4-chloro-5-(4- chlorophenyl)-2-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-3-carbonitrile

2.30 464.2 B 1.212 3-[4-[(3- benzylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.83 418.2 B 1.213 3-[4-[(3- benzylsulfanyl-1,2,4- triazol-4-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.89 418.2 B 1.214 5-methoxy-2-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine

1.24 341.1 B 1.215 5-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine

1.32 341.1 B 1.216 3-[4-[[4-chloro-5- (2,2-difluoro-1,3-benzodioxol-4-yl)-3- methyl-pyrazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.22 499.1 B 1.217 3-[4-[[4-chloro-3- (2,2-difluoro-1,3-benzodioxol-4-yl)-5- methyl-pyrazol-1- yl]methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

2.26 499.1 B 1.218 3-(4-chlorophenyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carbonitrile

2.07 430.1 B 1.219 ethyl 2-[1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-3-yl]pyridine-3-carboxylate

1.72 444.2 B 1.220 3-[4-[[4-chloro-5- (2,4-dichlorophenyl)- 3-(trifluoromethyl) pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

2.37 541.1 B 1.221 3-[4-[[4-chloro-3- (2,4-dichlorophenyl)- 5-(trifluoromethyl) pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

2.46 541.1 B 1.222 5-(difluoromethyl)-2- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine

1.38 361.1 B 1.223 5-(4- methoxyphenyl)-2- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-3- carbaldehyde

2.01 429.2 B 1.224 ethyl 5-propyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4- carboxylate

1.64 409.2 B 1.225 ethyl 5-propyl-3-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole-4- carboxylate

1.67 409.2 B 1.226 3-[4-(1,2,4-triazol-4- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.13 296.1 B 1.227 4-[2-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] tetrazol-5- yl]benzaldehyde

1.81 401.2 B 1.228 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] indazole-3-carbonitrile

1.91 370.1 B 1.229 3-[4-[[4-(4- chlorophenyl)imidazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.53 405.1 B 1.230 3-[4-[[5-(4- chlorophenyl)tetrazol-1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

1.81 407.1 B 1.231 3-[4-[[5-(4- chlorophenyl)tetrazol-2-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole

2.08 407.1 B 1.232 3-[4-[(5-bromo-3- methoxy-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.66 404.1 B 1.233 3-[4-[(3-bromo-5- methoxy-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.73 404.1 B 1.234 3-[4-[[5-(4-bromo-3- methyl- phenyl)tetrazol-1-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.94 465.1 B 1.235 3-[4-[[5-(4-bromo-3- methyl- phenyl)tetrazol-2-yl]methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

2.21 465.1 B 1.236 methyl 5- cyclopropyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

1.80 393.2 B 1.237 methyl 3- cyclopropyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

1.85 393.2 B 1.238 methyl 3- (methoxymethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate

1.60 397.2 B 1.239 methyl 5- (methoxymethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate

1.73 397.2 B 1.240 5-(2,6- difluorophenyl)-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carbonitrile

1.84 433.0 B 1.241 5-(2,6- difluorophenyl)-2-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carbonitrile

1.98 433.1 B 1.242 ethyl 3- (trifluoromethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate

1.93 435.2 B 1.243 3-[4-[(3- chloropyrazol-1- yl)methyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.75 329.1 B 1.244 3-[4-(triazolo[4,5- b]pyridin-4- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.11 347.1 B 1.245 3-[4-(triazolo[4,5- b]pyridin-1- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.42 347.1 B 1.246 3-[4-(triazolo[4,5- b]pyridin-2- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.56 347.1 B 1.247 3-[4-(triazolo[4,5- b]pyridin-3- ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.60 347.1 B 1.248 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

122- 129 1.249 N- (cyclopropylmethyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-

195- 200 carboxamide 1.250 N-(2-methoxyethyl)- 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide

132- 142 1.251 N-prop-2-ynyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

145- 155 1.252 ethyl 1-[[3-fluoro-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

131- 135 1.253 3-[4-[(3,5- dimethylpyrazol-1- yl)methyl]-2-fluoro-phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

1.08 341 A 1.254 3-[4-[(6-methoxy-3- pyridyl)methyl] phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

A 1.255 1-[[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile

120- 123 1.256 2-[[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile

1.03 337 (M − H) A 1.257 1-[[6-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]-3-pyridyl]methyl]- 1,2,4-triazole-3- carbonitrile

105- 108 1.258 2-[[6-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]-3-pyridyl]methyl]- 1,2,4-triazole-3- carbonitrile

0.89 322 A 1.259 N,N-diethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

86- 96 1.260 N-methoxy-N- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

102- 112 1.261 morpholino-[1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4-yl]methanone

125- 135 1.262 ~{tert}-butyl 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

81- 91 1.263 isopropyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4-carboxylate

1.13 381 A 1.264 propyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4-carboxylate

105- 115 1.265 2- (dimethylamino)ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate

60- 70 1.266 ~{N}-methoxy-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

128- 138 1.267 ~{N}-ethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4- carboxamide

166- 176 1.268 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4- carboxamide

0.86 338 A 1.269 ethyl 1-[[6-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]-3- pyridyl]methyl] pyrazole-4-carboxylate

88- 90 1.270 methyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxylate

154- 156 1.271 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxylic acid

208- 210 1.272 N-methyl-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxamide

0.92 352 C 1.273 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazole-4- carbaldehyde

91- 96 1.274 N-ethyl-1-[[4-(5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxamide

193- 195 1.275 N-methoxy-N- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide

135- 137 1.276 ethyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxylate

134- 136 1.277 N-methoxy-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxamide

198- 200 1.278 isopropyl 1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxylate

146- 148 1.279 methyl 3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxylate

103- 107 1.280 N,N-dimethyl-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide

168- 170 1.281 N-(4- methoxyphenyl)-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide

205- 207 1.282 N-(4-chlorophenyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide

233- 235 1.283 N-(4-pyridyl)-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide

204- 206 1.284 3-[5-[(3,5- dimethylpyrazol-1- yl)methyl]-2-pyridyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

0.95 324 A 1.285 N-methoxy-1-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4- yl]methanimine

88- 98 1.286 N-ethoxy-1-[1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrazol-4- yl]methanimine

80- 120 1.287 N-propoxy-1-[1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4- yl]methanimine

60- 95 1.288 N-isopropoxy-1-[1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4- yl]methanimine

1.14; 1.16 Mass not detected A 1.289 N-benzyloxy-1-[1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4-yl]methanimine

75- 85 1.290 N-prop-2-ynoxy-1-[1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazol-4- yl]methanimine

57- 63 1.291 N-methyl-3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] triazole-4-carboxamide

222- 224 1.292 N-methoxy-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrolidin-3-imine

1.10 341 B 1.293 N-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] piperidin-4-imine

1.04 355 B 1.294 3-[4-[(5- methylsulfonyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

119.2- 119.8 1.295 3-[4-[(5- methylsulfinyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

71.2- 73.7 1.296 3-[4-[(3- methylsulfonyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

145.4- 146.4 1.297 3-[4-[(3- methylsulfinyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

114.4- 115.2 1.298 3-[4-[(5- methylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

72- 73.2 1.299 3-[4-[(3- methylsulfanyl-1,2,4- triazol-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

88- 90.4 1.300 3-[4-(1- piperidylmethyl) phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole

0.75 313 A 1.301 4-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl] morpholine

0.68 315 A 1.302 3-[4- (thiomorpholino- methyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

54.5- 56.6 1.303 3-[4-[1-(3,5- dimethylpyrazol-1- yl)ethyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.61 337 C 1.304 ethyl 1-[1-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]ethyl] pyrazole-4-carboxylate

1.61 381 C 1.305 3-[4-[(4- methylsulfonyl- piperazin-1-yl)methyl]phenyl]-5- (trifluoromethyl)- 1,2,4-oxadiazole

111.1- 114.9 1.306 2,6-dimethyl-4-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] morpholine

0.76; 0.81 343 A 1.307 (2R,6S)-2,6- dimethyl-4-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] morpholine

0.76 343 A 1.308 (2R,6R)-2,6- dimethyl-4-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] morpholine

0.81 343 A 1.309 3-[4-[2-(3,5- dimethylpyrazol-1- yl)ethyl]phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole

1.67 337 C 1.310 ethyl 1-[2-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-yl]phenyl]ethyl] pyrazole-4-carboxylate

1.57 381 C 108- 110 1.311 ethyl 1-[2-fluoro-2- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl] pyrazole-4-carboxylate

145- 147 1.312 2-morpholino-2-[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetonitrile

1.07 339 A

BIOLOGICAL EXAMPLES

General Examples of Leaf Disk Tests in Well Plates:

Leaf disks or leaf segments of various plant species are cut from plantsgrown in a greenhouse. The cut leaf disks or segments are placed inmultiwell plates (24-well format) onto water agar. The leaf disks aresprayed with a test solution before (preventative) or after (curative)inoculation. Compounds to be tested are prepared as DMSO solutions (max.10 mg/ml) which are diluted to the appropriate concentration with 0.025%Tween20 just before spraying. The inoculated leaf disks or segments areincubated under defined conditions (temperature, relative humidity,light, etc.) according to the respective test system. A singleevaluation of disease level is carried out 3 to 14 days afterinoculation, depending on the pathosystem. Percent disease controlrelative to the untreated check leaf disks or segments is thencalculated.

General Examples of Liquid Culture Tests in Well Plates:

Mycelia fragments or conidia suspensions of a fungus prepared eitherfreshly from liquid cultures of the fungus or from cryogenic storage,are directly mixed into nutrient broth. DMSO solutions of the testcompound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of50 and 10 μl of this solution is pipetted into a microtiter plate(96-well format). The nutrient broth containing the fungalspores/mycelia fragments is then added to give an end concentration ofthe tested compound. The test plates are incubated in the dark at 24° C.and 96% relative humidity. The inhibition of fungal growth is determinedphotometrically after 2 to 7 days, depending on the pathosystem, andpercent antifungal activity relative to the untreated check iscalculated.

Example 1: Fungicidal Activity Against Puccinia recondita f. Sp.Tritici/Wheat/Leaf Disc Preventative (Brown Rust)

Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks were inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf segments wereincubated at 19° C. and 75% relative humidity (rh) under a light regimeof 12 hours light/12 hours darkness in a climate cabinet and theactivity of a compound was assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf segments (7 to 9 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9,1.10, 1.11, 1.12, 1.15, 1.16, 1.18, 1.19, 1.21, 1.22, 1.23, 1.24, 1.25,1.26, 1.27, 1.28, 1.29, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.37, 1.39,1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.52,1.53, 1.55, 1.56, 1.57, 1.58, 1.60, 1.61, 1.62, 1.63, 1.65, 1.67, 1.73,1.74, 1.75, 1.76, 1.79, 1.80, 1.81, 1.82, 1.83, 1.85, 1.86, 1.87, 1.88,1.89, 1.90, 1.91, 1.93, 1.94, 1.95, 1.96, 1.99, 1.101, 1.102, 1.105,1.107, 1.108, 1.109, 1.112, 1.118, 1.119, 1.120, 1.121, 1.122, 1.123,1.124, 1.125, 1.126, 1.128, 1.129, 1.131, 1.132, 1.133, 1.135, 1.136,1.137, 1.139, 1.141, 1.144, 1.145, 1.146, 1.147, 1.148, 1.149, 1.150,1.151, 1.154, 1.156, 1.157, 1.158, 1.171, 1.174, 1.186, 1.192, 1.193,1.200, 1.203, 1.204, 1.206, 1.207, 1.208, 1.209, 1.212, 1.213, 1.214,1.215, 1.219, 1.222, 1.224, 1.226, 1.229, 1.232, 1.233, 1.236, 1.237,1.238, 1.239, 1.240, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.249,1.250, 1.251, 1.252, 1.253, 1.254, 1.255, 1.256, 1.259, 1.260, 1.261,1.262, 1.263, 1.265, 1.266, 1.267, 1.268, 1.269, 1.270, 1.271, 1.273,1.274, 1.275, 1.276, 1.277, 1.278, 1.279, 1.280, 1.281, 1.282, 1.283,1.285, 1.286, 1.287, 1.288, 1.289, 1.290, 1.292, 1.294, 1.295, 1.296,1.297, 1.298, 1.299, 1.301, 1.302, 1.303, 1.304, 1.305, 1.306, 1.308,1.310 and 1.312.

Example 2: Fungicidal Activity Against Puccinia recondita f. Sp.Tritici/Wheat/Leaf Disc Curative (Brown Rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format). The leaf segments are then inoculated with a sporesuspension of the fungus. Plates were stored in darkness at 19° C. and75% relative humidity. The formulated test compound diluted in water wasapplied 1 day after inoculation. The leaf segments were incubated at 19°C. and 75% relative humidity under a light regime of 12 hours light/12hours darkness in a climate cabinet and the activity of a compound wasassessed as percent disease control compared to untreated when anappropriate level of disease damage appears in untreated check leafsegments (6 to 8 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.5, 1.6, 1.8, 1.9, 1.10, 1.11,1.15, 1.16, 1.18, 1.19, 1.22, 1.23, 1.25, 1.26, 1.27, 1.30, 1.32, 1.33,1.34, 1.35, 1.36, 1.38, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46,1.49, 1.54, 1.55, 1.56, 1.61, 1.62, 1.67, 1.71, 1.76, 1.77, 1.78, 1.79,1.80, 1.81, 1.82, 1.83, 1.85, 1.86, 1.87, 1.88, 1.89, 1.90, 1.91, 1.93,1.96, 1.97, 1.99, 1.101, 1.102, 1.118, 1.119, 1.120, 1.121, 1.123,1.124, 1.128, 1.129, 1.131, 1.132, 1.133, 1.134, 1.135, 1.136, 1.137,1.141, 1.143, 1.144, 1.145, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151,1.154, 1.156, 1.174, 1.192, 1.200, 1.203, 1.206, 1.207, 1.208, 1.209,1.213, 1.214, 1.215, 1.219, 1.222, 1.226, 1.229, 1.232, 1.233, 1.236,1.237, 1.238, 1.239, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.253,1.254, 1.255, 1.256, 1.258, 1.259, 1.260, 1.261, 1.263, 1.264, 1.265,1.266, 1.267, 1.268, 1.269, 1.270, 1.271, 1.272, 1.273, 1.274, 1.275,1.277, 1.279, 1.280, 1.281, 1.283, 1.285, 1.287, 1.288, 1.290, 1.291,1.292, 1.293, 1.294, 1.295, 1.296, 1.297, 1.298, 1.299, 1.302 1.303,1.304, 1.305, 1.306 and 1.312.

Example 3: Fungicidal Activity Against Phakopsorapachyrhizi/Soybean/Leaf Disc Preventative (Asian Soybean Rust)

Soybean leaf disks are placed on water agar in multiwell plates (24-wellformat) and sprayed with the formulated test compound diluted in water.One day after application leaf discs are inoculated by spraying a sporesuspension on the lower leaf surface. After an incubation period in aclimate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leafdisc are kept at 20° C. with 12 h light/day and 75% rh. The activity ofa compound is assessed as percent disease control compared to untreatedwhen an appropriate level of disease damage appears in untreated checkleaf disks (12 to 14 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.9, 1.10,1.11, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.24, 1.25,1.26, 1.27, 1.28, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.39, 1.40, 1.41,1.42, 1.43, 1.49, 1.56, 1.59, 1.61, 1.79, 1.85, 1.86, 1.87, 1.88, 1.90,1.91, 1.93, 1.96, 1.99, 1.101, 1.102, 1.129, 1.136, 1.146, 1.147, 1.148,1.149, 1.150, 1.151, 1.152, 1.153, 1.154, 1.156, 1.157, 1.158, 1.171,1.174, 1.177, 1.184, 1.185, 1.186, 1.187, 1.190, 1.192, 1.193, 1.194,1.195, 1.198, 1.200, 1.201, 1.203, 1.204, 1.205, 1.206, 1.207, 1.208,1.209, 1.212, 1.213, 1.214, 1.215, 1.219, 1.222, 1.223, 1.224, 1.226,1.227, 1.228, 1.229, 1.230, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239,1.240, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.252, 1.253, 1.256,1.259, 1.260, 1.261, 1.263, 1.264, 1.265, 1.266, 1.267, 1.268, 1.270,1.273, 1.274, 1.275, 1.276, 1.277, 1.278, 1.279, 1.280, 1.283, 1.285,1.286, 1.288, 1.290, 1.303, 1.304, 1.305, 1.306, 1.310 and 1.312.

Example 4: Fungicidal Activity Against Glomerella Lagenarium(Colletotrichum Lagenarium) Liquid Culture/Cucumber/Preventative(Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB—potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3 to 4 days after application.

The following compounds at 20 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol under the same conditions, which show extensive diseasedevelopment.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9,1.10, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.24, 1.25,1.26, 1.27, 1.28, 1.29, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.37, 1.38,1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50,1.51, 1.52, 1.54, 1.55, 1.56, 1.57, 1.58, 1.59, 1.60, 1.61, 1.62, 1.63,1.64, 1.65, 1.66, 1.67, 1.68, 1.69, 1.70, 1.72, 1.73, 1.74, 1.75, 1.76,1.77, 1.79, 1.80, 1.81, 1.82, 1.83, 1.84, 1.85, 1.86, 1.87, 1.88, 1.89,1.90, 1.91, 1.92, 1.93, 1.94, 1.95, 1.96, 1.97, 1.98, 1.99, 1.100,1.101, 1.102, 1.103, 1.104, 1.106, 1.107, 1.108, 1.109, 1.110, 1.111,1.112, 1.113, 1.114, 1.115, 1.116, 1.117, 1.118, 1.119, 1.120, 1.121,1.122, 1.124, 1.126, 1.127, 1.128, 1.129, 1.130, 1.131, 1.132, 1.133,1.135, 1.136, 1.137, 1.138, 1.140, 1.142, 1.143, 1.144, 1.146, 1.147,1.148, 1.149, 1.150, 1.151, 1.152, 1.154, 1.157, 1.158, 1.171, 1.174,1.184, 1.185, 1.186, 1.188, 1.189, 1.190, 1.191, 1.192, 1.193, 1.194,1.198, 1.200, 1.203, 1.204, 1.205, 1.206, 1.207, 1.208, 1.209, 1.212,1.213, 1.214, 1.215, 1.219, 1.222, 1.223, 1.224, 1.226, 1.227, 1.228,1.229, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239, 1.240, 1.243, 1.244,1.245, 1.246, 1.247, 1.248, 1.249, 1.250, 1.251, 1.252, 1.253, 1.254,1.255, 1.256, 1.257, 1.258, 1.259, 1.260, 1.261, 1.262, 1.263, 1.264,1.265, 1.266, 1.267, 1.268, 1.269, 1.270, 1.273, 1.274, 1.275, 1.276,1.277, 1.278, 1.279, 1.280, 1.281, 1.283, 1.284, 1.285, 1.286, 1.287,1.288, 1.289, 1.290, 1.292, 1.294, 1.295, 1.296, 1.297, 1.298, 1.2991.302. 1.303, 1.304, 1.305, 1.306, 1.307, 1.309 and 1.312.

Example 5: Fungicidal Activity Against Uromyces viciae-Fabael FieldBean/Leaf Disc Preventative (Faba-Bean Rust)

Field bean leaf discs are placed on water agar in multiwell plates(96-well format) and 10 μl of the formulated test compound diluted inacetone and a spreader pipetted onto the leaf disc. Two hours afterapplication leaf discs are inoculated by spraying a spore suspension onthe lower leaf surface. The leaf discs are incubated in a climatecabinet at 22° C. with 18 hour day and 70% relative humidity. Theactivity of a compound is assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf disks (12 days after application).

The following compounds at 100 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf discs under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9,1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, and 1.20.

1. A compound of formula (I):

wherein n is 1 or 2; A¹ represents N or CR¹, wherein R¹ represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; A² represents N or CR², wherein R² represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; A³ represents N or CR³, wherein R³ represents hydrogen or halogen; A⁴ represents N or CR⁴, wherein R⁴ represents hydrogen or halogen; and wherein 0 or 1 or 2 of A¹, A², A³ and A⁴ are N; R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, or R⁵ and R⁶ together with the carbon atom they share form a cyclopropyl; Z is selected from Z¹, Z², Z³, Z⁴, Z⁵ or Z⁶; wherein Z¹ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—C bond, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which contains 1 nitrogen in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, NR⁷, C(O), or S(O)₂, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; Z² represents a heteroaryl linked to C(R⁵)(R⁶) via a C—C bond, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which contains 1 nitrogen atom in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, or NR⁷; R⁷ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl, C₁₋₄alkylsulfonyl, N—C₁₋₂alkylaminosulfonyl, or N,N-diC₁₋₂alkylaminosulfonyl; and wherein for Z¹ and Z², the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁸; R⁸ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl or C₁₋₄alkoxycarbonylamino; Z³ represents a heterocyclyl linked to C(R⁵)(R⁶) via a C—N bond, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which contains 1 nitrogen in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, NR⁹ or C(═N—O—C₁₋₄alkyl), with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; Z⁴ represents a heteroaryl linked to C(R⁵)(R⁶) via a C—N bond, wherein the heteroaryl moiety is a 5-membered aromatic ring which contains 1 to 4 nitrogen atoms in the ring system; R⁹ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, or N,N-diC₁₋₄alkylaminocarbonyl; and wherein for Z³ and Z⁴, the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R¹⁰; wherein R¹⁰ represents: (i) cyano, halogen, hydroxy, amino, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄alkoxyC₁₋₄alkyl, C₁₋₄haloalkoxy, C₁₋₄alkylsulfanyl, C₁₋₄alkylsulfinyl, C₁₋₄alkylsulfonyl, C₁₋₄haloalkylsulfanyl, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, formyl, hydroxycarbonyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino, aminocarbonyl, N—C₁₋₄alkylaminocarbonyl, N—C₂₋₄alkenylaminocarbonyl, N—C₂₋₄alkynylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl, N-morpholinoaminocarbonyl, N—C₁₋₄alkoxyaminocarbonyl, N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl, C₁₋₄alkoxycarbonylamino, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl, phenylcarbonyloxyC₁₋₄alkyl, phenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxy, C₁₋₄haloalkylcarbonyloxy, C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, or (C₁₋₄alkyl)₃Si—; or (ii) —C(O)N(R^(a))(R^(b)), wherein: R^(a) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₅alkenyl, C₃₋₅alkynyl, aminoC₁₋₄alkyl, N—C₁₋₄alkylaminoC₁₋₄alkyl, N,N-diC₁₋₄alkylaminoC₁₋₄alkyl, formyl, C₁₋₄alkylcarbonyl, C₃₋₄cycloalkylcarbonyl, C₁₋₄haloalkylcarbonyl, C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₄alkyl, N,N-diC₁₋₄alkylaminocarbonylC₁₋₄alkyl, C₁₋₄alkylsulfanylC₁₋₄alkyl, C₁₋₄alkylsulfonyl, C₁₋₄alkylsulfonylC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, or C₁₋₄haloalkylcarbonylaminoC₁₋₄alkyl, and R^(b) is hydrogen, hydroxyl, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl, C₃₋₄cycloalkyl, C₃₋₄cycloalkylC₁₋₂alkyl, C₁₋₄alkoxy, C₃₋₄alkenyloxy, C₃₋₄haloalkenyloxy, or C₃₋₄alkynyloxy; or R^(a) and R^(b) together with the nitrogen atom to which they are bonded, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O)₂, C(O) and NR^(c), wherein R^(c) is hydrogen, methyl, methoxy, formyl or acyl; or (iii) —C(O)O—R^(d), wherein: R^(d) is hydrogen, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄cyanoalkyl, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₅alkenyl, C₃₋₄haloalkenyl, C₃₋₄ alkenyloxyC₁₋₄alkyl, C₃₋₅alkynyl, C₃₋₄alkynyloxyC₁₋₄alkyl, N—C₁₋₃alkylaminoC₁₋₄alkyl, N,N-di-C₁₋₃alkylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl or C₁₋₄alkylcarbonylaminoC₁₋₄alkyl; or wherein for Z⁴, the heteroaryl moiety is optionally substituted by 1 substituent selected from R¹¹ and further optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R¹⁰; wherein R¹¹ represents: (i) C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl, N—C₃₋₈cycloalkylaminocarbonyl, N—C₃₋₈cycloalkylC₁₋₂alkylaminocarbonyl, phenyl, phenylC₁₋₂alkyl, phenoxyC₁₋₂alkyl, phenylC₁₋₂alkylsulfanyl, heteroaryl, heteroarylC₁₋₂alkyl, heteroaryloxyC₁₋₂alkyl, N-heteroarylaminocarbonyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁₋₆alkyl, heterocyclylcarbonyl wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, benzodioxolyl, and wherein any of said cycloalkyl, phenyl, heteroaryl, heterocyclyl and benzodioxolyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R¹²; or (ii) —C(O)N(R^(e))(R^(f)), wherein: R^(e) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O)₂, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 groups which are oxo (═O), and R^(f) is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy C₁₋₄haloalkyl, C₃₋₄alkenyl, C₃₋₄alkynyl, C₃₋₄cycloalkyl, or C₃₋₄cycloalkylC₁₋₂alkyl; or (iii) —C(O)O—R^(g), wherein: R^(g) is C₃₋₅cycloalkyl, C₃₋₅cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₂alkyl, heterocyclyl, heterocyclylC₁₋₂alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O)₂, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 groups which are oxo (═O); or (iv) (C₁₋₄alkyl)-O—N═C(R^(h))—, (C₁₋₄haloalkyl)-O—N═C(R^(h))—, (C₂₋₄alkenyl)-O—N═C(R^(h)), (C₂₋₄alkynyl)-O—N═C(R^(h))—, benzyl-O—N═C(R^(h))—, wherein R^(h) is hydrogen or methyl; R¹² is cyano, fluoro, chloro, bromo, methyl, ethyl, formyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy or ethoxycarbonyl; Z⁵ represents a heterobicyclyl linked to C(R⁵)(R⁶) via a C—N bond, wherein the heterobicyclyl moiety is a 7- to 10-membered saturated, partially saturated or partially aromatic fused ring system which contains 1 nitrogen in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, NR¹³, C(O) or S(O)₂, with the proviso that the heterobicyclyl cannot contain 2 contiguous atoms selected from O and S; Z⁶ represents a heterodiaryl linked to C(R⁵)(R⁶) via a C—N bond, wherein the heterdioaryl moiety is a 9-membered di-aromatic system which contains 1 to 4 nitrogen atoms in the ring system; R¹³ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxy, formyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, N—C₁₋₄alkylaminocarbonyl, or N,N-diC₁₋₄alkylaminocarbonyl; and wherein for Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety is optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R¹⁴; R¹⁴ is cyano, halogen, hydroxy, formyl, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, cyanoC₁₋₄alkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylcarbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl or C₁₋₄alkoxycarbonylamino, and additionally oxo (═O) for Z⁵; or wherein for Z⁵ and Z⁶, the heterobicyclyl or heterodiaryl moiety is optionally substituted by 1 substituent selected from R¹⁵ and further optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R¹⁴; R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, wherein phenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and ethoxy; or a salt or an N-oxide thereof.
 2. A compound according to claim 1, wherein A¹ is N or CR¹ wherein R¹ is hydrogen, chloro, fluoro, methyl, methoxy or trifluoromethyl, and A², A³ and A⁴ are C—H.
 3. A compound according to claim 1, wherein A¹, A², A³ and A⁴ are C—H.
 4. A compound according to claim 1, wherein A³ is CR³ and R³ is halogen, and A¹, A² and A⁴ are C—H.
 5. A compound according to claim 1, wherein R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl.
 6. A compound according to claim 1, wherein Z is Z⁴.
 7. A compound according to claim 6, wherein the heteroaryl moiety of Z⁴ is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R¹⁰; R¹⁰ is cyano, halogen, hydroxy, amino, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄alkoxy, C₁₋₄alkoxyC₁₋₄alkyl, C₁₋₄alkylsulfanyl, C₁₋₄haloalkylsulfanyl, N,N-diC₁₋₄alkylamino, formyl, hydroxycarbonyl, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₃₋₄alkenyloxycarbonyl, C₃₋₄alkynyloxycarbonyl, aminocarbonyl, N—C₁₋₄alkylaminocarbonyl, N—C₃₋₄alkenylaminocarbonyl, N—C₂₋₄alkynylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl, N-morpholinoaminocarbonyl, N—C₁₋₄alkoxyaminocarbonyl, N—C₁₋₄alkyl-N—C₁₋₄alkoxyaminocarbonyl, N—C₁₋₄alkoxyC₁₋₄alkylaminocarbonyl, phenylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylcarbonylaminoC₁₋₄alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₄alkyl, or (C₁₋₄alkyl)₃Si—; or Z⁴ is optionally substituted by 1 substituent selected from R¹¹ and further optionally substituted by 1 or 2 substituents selected from R¹⁰; wherein R¹¹ is C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl, N—C₃₋₆cycloalkylaminocarbonyl, N—C₃₋₆cycloalkylC₁₋₂alkylaminocarbonyl, C₃₋₄cycloalkoxycarbonyl, C₃₋₄cycloalkylC₁₋₂alkoxycarbonyl, phenyl, phenylC₁₋₂alkyl, phenoxyC₁₋₂alkyl, phenylC₁₋₂alkylsulfanyl, N-phenylaminocarbonyl, heterocyclyl, heterocyclylcarbonyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O)₂, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC₁₋₂alkyl, heteroaryloxyC₁₋₂alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, benzodioxolyl, and wherein any of said cycloalkyl, phenyl, heterocyclyl, heteroaryl and benzodioxolyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R¹²; and R¹² is fluoro, chloro, bromo, methyl, ethyl, or methoxy.
 8. A compound according to claim 1, wherein Z⁴ is pyrazolyl, imidazolyl or triazolyl, wherein pyrazolyl, imidazolyl or triazolyl are optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R¹⁰; or pyrazolyl, imidazolyl or triazolyl are optionally substituted by 1 substituent selected from R¹¹ and are further optionally substituted by 1 substituent selected from R¹⁰.
 9. A compound according to claim 8, wherein Z⁴ is pyrazol-1-yl, 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl, wherein pyrazol-1-yl is optionally substituted by 1 substituent selected from R¹⁰ or R¹¹, wherein R¹⁰ is hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, methoxyethylaminocarbonyl, propargylaminocarbonyl, N-morpholinoaminocarbonyl, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N-methyl-N-methoxyaminocarbonyl or N-methoxyaminocarbonyl, and R¹¹ is cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl or cyclohexylaminocarbonyl; and 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl is optionally substituted by 1 substituent selected from R¹⁰ or R¹¹, wherein R¹⁰ is cyano, ethynyl, fluoro, chloro, methyl, ethyl, trifluoromethyl, methoxy, ethoxycarbonyl or ethoxymethyl, and R¹¹ is cyclopropyl.
 10. A compound according to claim 1, wherein Z is Z⁶ selected from indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl.
 11. A compound according to claim 10, wherein: indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R¹⁴, wherein R¹⁴ is cyano, halogen, hydroxy, formyl, C₁₋₄alkyl, C₁₋₄haloalkyl, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl, or C₁₋₄alkoxycarbonyl; or indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl is optionally substituted by 1 substituent selected from R¹⁵ and further optionally substituted by 1 or 2 substituents selected from R¹⁴, wherein R¹⁵ is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, wherein phenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and ethoxy.
 12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim
 1. 13. The composition according to claim 12, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.
 14. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to any of claim 1, or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
 15. Use of a compound of formula (I) according to any one of claim 1 as a fungicide. 